Franke, R., Selent, D. & Börner, A. Applied hydroformylation. Chem. Rev. 112, 5675–5732 (2012).Article
CAS
PubMed
Google Scholar
Deng, Y., Wang, H., Sun, Y. & Wang, X. Principles and applications of enantioselective hydroformylation of terminal disubstituted alkenes. ACS Catal. 5, 6828–6837 (2015).Article
CAS
Google Scholar
Klosin, J. & Landis, C. R. Ligands for practical rhodium-catalyzed asymmetric hydroformylation. Acc. Chem. Res. 40, 1251–1259 (2007).Article
CAS
PubMed
Google Scholar
Brezny, A. C. & Landis, C. R. Recent developments in the scope, practicality, and mechanistic understanding of enantioselective hydroformylation. Acc. Chem. Res. 51, 2344–2354 (2018).Article
CAS
PubMed
Google Scholar
Breit, B. Synthetic aspects of stereoselective hydroformylation. Acc. Chem. Res. 36, 264–275 (2003).Article
CAS
PubMed
Google Scholar
Ning, Y., Ohwada, T. & Chen, F.-E. Transition metal-catalyzed branch-selective hydroformylation of olefins in organic synthesis. Green. Synth. Catal. 2, 247–266 (2021).Article
Google Scholar
Jia, X., Wang, Z., Xia, C. & Ding, K. Recent advances in rh-catalyzed asymmetric hydroformylation of olefins. Chin. J. Org. Chem. 33, 1369–1381 (2013).Article
CAS
Google Scholar
Fernández-Pérez, H., Etayo, P., Panossian, A. & Vidal-Ferran, A. Phosphine-phosphinite and phosphine-phosphite ligands: preparation and applications in asymmetric catalysis. Chem. Rev. 111, 2119–2176 (2011).Article
PubMed
Google Scholar
Chikkali, S. H., van der Vlugt, J. I. & Reek, J. N. H. Hybrid diphosphorus ligands in rhodium catalysed asymmetric hydroformylation. Coord. Chem. Rev. 262, 1–15 (2014).Article
CAS
Google Scholar
Chakrabortty, S., Almasalma, A. A. & de Vries, J. G. Recent developments in asymmetric hydroformylation. Catal. Sci. Technol. 11, 5388–5411 (2021).Article
CAS
Google Scholar
Sakai, N., Mano, S., Nozaki, K. & Takaya, H. Highly enantioselective hydroformylation of olefins catalyzed by new phosphinephosphite-rh(i) complexes. J. Am. Chem. Soc. 115, 7033–7034 (1993).Article
CAS
Google Scholar
Buisman, G. J. H., Vos, E. J., Kamer, P. C. J. & van Leeuwen, P. W. N. M. Hydridorhodium diphosphite catalysts in the asymmetric hydroformylation of styrene. J. Chem. Soc., Dalton Trans. 409–417 (1995).Clark, T. P., Landis, C. R., Freed, S. L., Klosin, J. & Abboud, K. A. Highly active, regioselective, and enantioselective hydroformylation with Rh catalysts ligated by Bis-3,4-diazaphospholanes. J. Am. Chem. Soc. 127, 5040–5042 (2005).Article
CAS
PubMed
Google Scholar
Axtell, A. T. et al. Highly regio- and enantioselective asymmetric hydroformylation of olefins mediated by 2,5-disubstituted phospholane ligands. Angew. Chem. Int. Ed. 44, 5834–5838 (2005).Article
CAS
Google Scholar
Yan, Y. & Zhang, X. A hybrid phosphorus ligand for highly enantioselective asymmetric hydroformylation. J. Am. Chem. Soc. 128, 7198–7202 (2006).Article
CAS
PubMed
Google Scholar
Zhang, D., Wen, J. & Zhang, X. Construction of a quaternary stereogenic center by asymmetric hydroformylation: a straightforward method to prepare chiral alpha-quaternary amino acids. Chem. Sci. 13, 7215–7223 (2022).Article
CAS
PubMed
PubMed Central
Google Scholar
Noonan, G. M., Fuentes, J. A., Cobley, C. J. & Clarke, M. L. An asymmetric hydroformylation catalyst that delivers branched aldehydes from alkyl alkenes. Angew. Chem. Int. Ed. 51, 2477–2480 (2012).Article
CAS
Google Scholar
Schmitz, C., Holthusen, K., Leitner, W. & Franciò, G. Highly regio- and enantioselective hydroformylation of vinyl esters using bidentate phosphine, p-chiral phosphorodiamidite ligands. ACS Catal. 6, 1584–1589 (2016).Article
CAS
Google Scholar
Chikkali, S. H., Bellini, R., de Bruin, B., van der Vlugt, J. I. & Reek, J. N. Highly selective asymmetric Rh-catalyzed hydroformylation of heterocyclic olefins. J. Am. Chem. Soc. 134, 6607–6616 (2012).Article
CAS
PubMed
Google Scholar
Wang, X. & Buchwald, S. L. Rh-catalyzed asymmetric hydroformylation of functionalized 1,1-disubstituted olefins. J. Am. Chem. Soc. 133, 19080–19083 (2011).Article
CAS
PubMed
Google Scholar
Breeden, S., Cole-Hamilton, D. J., Foster, D. F., Schwarz, G. J. & Wills, M. Rhodium-mediated asymmetric hydroformylation with a novel Bis(diazaphospholidine) Ligand. Angew. Chem. Int. Ed. 39, 4106–4108 (2000).Article
ADS
CAS
Google Scholar
Jouffroy, M. et al. Confining phosphanes derived from cyclodextrins for efficient regio- and enantioselective hydroformylation. Angew. Chem. Int. Ed. 53, 3937–3940 (2014).Article
CAS
Google Scholar
Franciò, G., Faraone, F. & Leitner, W. Asymmetric catalysis with chiral phosphane/ phosphoramidite ligands derived from quinoline (QUINAPHOS). Angew. Chem. Int. Ed. 39, 1428–1430 (2000).Article
Google Scholar
Zhao, B., Peng, X., Wang, Z., Xia, C. & Ding, K. Modular chiral bidentate phosphonites: design, synthesis, and application in catalytic asymmetric hydroformylation reactions. Chem. Eur. J. 14, 7847–7857 (2008).Article
CAS
PubMed
Google Scholar
Eshon, J., Foarta, F., Landis, C. R. & Schomaker, J. M. α-tetrasubstituted aldehydes through electronic and strain-controlled branch-selective stereoselective hydroformylation. J. Org. Chem. 83, 10207–10220 (2018).Article
CAS
PubMed
PubMed Central
Google Scholar
Li, S., Zhang, D., Zhang, R., Bai, S. T. & Zhang, X. Rhodium-catalyzed chemo-, regio- and enantioselective hydroformylation of cyclopropyl-functionalized trisubstituted alkenes. Angew. Chem. Int. Ed. 61, e202206577 (2022).Article
ADS
CAS
Google Scholar
Clarke, M. L. & Roff, G. J. Highly regioselective rhodium-catalysed hydroformylation of unsaturated esters: the first practical method for quaternary selective carbonylation. Chem. Eur. J. 12, 7978–7986 (2006).Article
CAS
PubMed
Google Scholar
Lebel, H., Marcoux, J.-F., Molinaro, C. & Charette, A. B. Stereoselective cyclopropanation reactions. Chem. Rev. 103, 977–1050 (2003).Article
CAS
PubMed
Google Scholar
Reissig, H.-U. & Zimmer, R. Donor-acceptor-substituted cyclopropane derivatives and their application in organic synthesis. Chem. Rev. 103, 1151–1196 (2003).Article
CAS
PubMed
Google Scholar
Wessjohann, L. A. & Brandt, W. Biosynthesis and metabolism of cyclopropane rings in natural compounds. Chem. Rev. 103, 1625–1647 (2003).Article
CAS
PubMed
Google Scholar
Talele, T. T. The “Cyclopropyl Fragment” is a versatile player that frequently appears in preclinical/clinical drug molecules. J. Med. Chem. 59, 8712–8756 (2016).Article
ADS
CAS
PubMed
Google Scholar
Ebner, C. & Carreira, E. M. Cyclopropanation strategies in recent total syntheses. Chem. Rev. 117, 11651–11679 (2017).Article
CAS
PubMed
Google Scholar
Dian, L. & Marek, I. Asymmetric preparation of polysubstituted cyclopropanes based on direct functionalization of achiral three-membered carbocycles. Chem. Rev. 118, 8415–8434 (2018).Article
CAS
PubMed
Google Scholar
Wu, W., Lin, Z. & Jiang, H. Recent advances in the synthesis of cyclopropanes. Org. Biomol. Chem. 16, 7315–7329 (2018).Article
CAS
PubMed
Google Scholar
Pons, A., Delion, L., Poisson, T., Charette, A. B. & Jubault, P. Asymmetric synthesis of fluoro, fluoromethyl, difluoromethyl, and trifluoromethylcyclopropanes. Acc. Chem. Res. 54, 2969–2990 (2021).Article
CAS
PubMed
Google Scholar
Simmons, H. E. & Smith, R. D. A new synthesis of cyclopropanes from olefins. J. Am. Chem. Soc. 80, 5323–5324 (1958).Article
CAS
Google Scholar
Simmons, H. E. & Smith, R. D. A new synthesis of cyclopropanes. J. Am. Chem. Soc. 81, 4256–4264 (1959).Article
CAS
Google Scholar
Shen, J. J. et al. Enantioselective iron-catalyzed intramolecular cyclopropanation reactions. Angew. Chem. Int. Ed. 53, 13188–13191 (2014).Article
CAS
Google Scholar
Coelho, P. S., Brustad, E. M., Kannan, A. & Arnold, F. H. Olefin cyclopropanation via carbene transfer catalyzed by engineered cytochrome P450 enzymes. Science 339, 307–310 (2013).Article
ADS
CAS
PubMed
Google Scholar
Rubina, M., Rubin, M. & Gevorgyan, V. Catalytic enantioselective hydroboration of cyclopropenes. J. Am. Chem. Soc. 125, 7198–7199 (2003).Article
CAS
PubMed
Google Scholar
Sherrill, W. M. & Rubin, M. Rhodium-catalyzed hydroformylation of cyclopropenes. J. Am. Chem. Soc. 130, 13804–13809 (2008).Article
CAS
PubMed
Google Scholar
Coulter, M. M., Kou, K. G., Galligan, B. & Dong, V. M. Regio- and enantioselective intermolecular hydroacylation: substrate-directed addition of salicylaldehydes to homoallylic sulfides. J. Am. Chem. Soc. 132, 16330–16333 (2010).Article
CAS
PubMed
Google Scholar
Liu, F., Bugaut, X., Schedler, M., Fröhlich, R. & Glorius, F. Designing N-heterocyclic carbenes: simultaneous enhancement of reactivity and enantioselectivity in the asymmetric hydroacylation of cyclopropenes. Angew. Chem. Int. Ed. 50, 12626–12630 (2011).Article
CAS
Google Scholar
Parra, A. et al. Copper-catalyzed diastereo- and enantioselective desymmetrization of cyclopropenes: synthesis of cyclopropylboronates. J. Am. Chem. Soc. 136, 15833–15836 (2014).Article
CAS
PubMed
Google Scholar
Teng, H.-L. et al. Synthesis of chiral aminocyclopropanes by rare-earth-metal-catalyzed cyclopropene hydroamination. Angew. Chem. Int. Ed. 55, 15406–15410 (2016).Article
CAS
Google Scholar
Luo, Y., Teng, H. L., Nishiura, M. & Hou, Z. Asymmetric Yttrium-Catalyzed C(sp(3))-H addition of 2-methyl azaarenes to cyclopropenes. Angew. Chem. Int. Ed. 56, 9207–9210 (2017).Article
CAS
Google Scholar
Teng, H. L., Luo, Y., Nishiura, M. & Hou, Z. Diastereodivergent asymmetric carboamination/annulation of cyclopropenes with aminoalkenes by chiral lanthanum catalysts. J. Am. Chem. Soc. 139, 16506–16509 (2017).Article
CAS
PubMed
Google Scholar
Dian, L. & Marek, I. Rhodium-catalyzed arylation of cyclopropenes based on asymmetric direct functionalization of three-membered carbocycles. Angew. Chem. Int. Ed. 57, 3682–3686 (2018).Article
CAS
Google Scholar
Sommer, H. & Marek, I. Diastereo- and enantioselective copper catalyzed hydroallylation of disubstituted cyclopropenes. Chem. Sci. 9, 6503–6508 (2018).Article
CAS
PubMed
PubMed Central
Google Scholar
Teng, H.-L., Ma, Y., Zhan, G., Nishiura, M. & Hou, Z. Asymmetric C(sp)–H addition of terminal alkynes to cyclopropenes by a chiral gadolinium catalyst. ACS Catal. 8, 4705–4709 (2018).Article
CAS
Google Scholar
Zhang, H., Huang, W., Wang, T. & Meng, F. Cobalt-catalyzed diastereo- and enantioselective hydroalkenylation of cyclopropenes with alkenylboronic acids. Angew. Chem. Int. Ed. 58, 11049–11053 (2019).Article
CAS
Google Scholar
Zhao, Z.-Y. et al. Enantioselective rhodium-catalyzed desymmetric hydrosilylation of cyclopropenes. ACS Catal. 9, 9110–9116 (2019).Article
CAS
Google Scholar
Dian, L. & Marek, I. Pd-catalyzed enantioselective hydroalkynylation of cyclopropenes. ACS Catal. 10, 1289–1293 (2020).Article
CAS
PubMed
Google Scholar
Huang, W. & Meng, F. Cobalt-catalyzed diastereo- and enantioselective hydroalkylation of cyclopropenes with cobalt homoenolates. Angew. Chem. Int. Ed. 60, 2694–2698 (2021).Article
CAS
Google Scholar
Nie, S., Lu, A., Kuker, E. L. & Dong, V. M. Enantioselective hydrothiolation: diverging cyclopropenes through ligand control. J. Am. Chem. Soc. 143, 6176–6184 (2021).Article
CAS
PubMed
PubMed Central
Google Scholar
Huang, Q., Chen, Y., Zhou, X., Dai, L. & Lu, Y. Nickel-hydride-catalyzed diastereo- and enantioselective hydroalkylation of cyclopropenes. Angew. Chem. Int. Ed. 61, e202210560 (2022).Article
CAS
Google Scholar
Cai, S.-Z. et al. Nickel-catalyzed enantioselective hydrothiocarbonylation of cyclopropenes. Org. Lett. 25, 8683–8687 (2023).Article
CAS
PubMed
Google Scholar
Daniels, B. S. et al. Copper-phosphido catalysis: enantioselective addition of phosphines to cyclopropenes. Angew. Chem. Int. Ed. 62, e202306511 (2023).Article
CAS
Google Scholar
Lin, X. et al. Diastereo- and enantioselective hydrophosphination of cyclopropenes under lanthanocene catalysis. Angew. Chem. Int. Ed. 62, e202308488 (2023).Article
ADS
CAS
Google Scholar
Zhang, S., Jiang, N., Xiao, J.-Z., Lin, G.-Q. & Yin, L. Copper(I)-catalyzed asymmetric hydrophosphination of 3,3-disubstituted cyclopropenes. Angew. Chem. Int. Ed. 62, e202218798 (2023).Article
CAS
Google Scholar
Zhang, Z.-L. et al. Cobalt-catalyzed facial-selective hydroalkylation of cyclopropenes. Angew. Chem. Int. Ed. 62, e202306381 (2023).Article
CAS
Google Scholar
Sunoj, R. B. Transition state models for understanding the origin of chiral induction in asymmetric catalysis. Acc. Chem. Res. 49, 1019–1028 (2016).Article
CAS
PubMed
Google Scholar
Dangat, Y., Popli, S. & Sunoj, R. B. Unraveling the Importance of Noncovalent Interactions in Asymmetric Hydroformylation Reactions. J. Am. Chem. Soc. 142, 17079–17092 (2020).Article
CAS
PubMed
Google Scholar
Ghosh, S. et al. Role of noncovalent interactions in inducing high enantioselectivity in an alcohol reductive deoxygenation reaction involving a planar carbocationic intermediate. J. Am. Chem. Soc. 145, 2884–2900 (2023).Article
CAS
PubMed
Google Scholar
Lei, M., Wang, Z., Du, X., Zhang, X. & Tang, Y. Asymmetric hydroformylation catalyzed by RhH(CO)2[(R,S)-Yanphos]: mechanism and origin of enantioselectivity. J. Phys. Chem. A. 118, 8960–8970 (2014).Article
CAS
PubMed
Google Scholar
Szlapa, E. N. & Harvey, J. N. Computational modelling of selectivity in cobalt-catalyzed propene hydroformylation. Chem. Eur. J. 24, 17096–17104 (2018).Article
CAS
PubMed
Google Scholar
Zhang, X. et al. Synthesis and application of modular phosphine-phosphoramidite ligands in asymmetric hydroformylation: structure-selectivity relationship. Chem. Eur. J. 16, 871–877 (2010).Article
CAS
PubMed
Google Scholar
Wei, B., Chen, C., You, C., Lv, H. & Zhang, X. Efficient synthesis of (S,R)-Bn-Yanphos and Rh/(S,R)-Bn-Yanphos catalyzed asymmetric hydroformylation of vinyl heteroarenes. Org. Chem. Front. 4, 288–291 (2017).Article
CAS
Google Scholar
You, C. et al. Design and application of hybrid phosphorus ligands for enantioselective rh-catalyzed anti-markovnikov hydroformylation of unfunctionalized 1,1-disubstituted alkenes. J. Am. Chem. Soc. 140, 4977–4981 (2018).Article
CAS
PubMed
Google Scholar
You, C., Li, S., Li, X., Lv, H. & Zhang, X. Enantioselective Rh-catalyzed anti-markovnikov hydroformylation of 1,1-disubstituted allylic alcohols and amines: an efficient route to chiral lactones and lactams. ACS Catal. 9, 8529–8533 (2019).Article
CAS
Google Scholar
Li, S. et al. Rhodium-catalyzed enantioselective anti-markovnikov hydroformylation of α-substituted acryl acid derivatives. Org. Lett. 22, 1108–1112 (2020).Article
CAS
PubMed
Google Scholar
Zhang, D., You, C., Li, X., Wen, J. & Zhang, X. Asymmetric linear-selective hydroformylation of 1,1-dialkyl olefins assisted by a steric-auxiliary strategy.Org. Lett. 22, 4523–4526 (2020).Article
ADS
CAS
PubMed
Google Scholar
Iu, L., Fuentes, J. A., Janka, M. E., Fontenot, K. J. & Clarke, M. L. High iso aldehyde selectivity in the hydroformylation of short-chain alkenes. Angew. Chem. Int. Ed. 58, 2120–2124 (2019).Article
CAS
Google Scholar
Jongkind, L. J., Elemans, J. & Reek, J. N. H. Cofactor controlled encapsulation of a rhodium hydroformylation catalyst. Angew. Chem. Int. Ed. 58, 2696–2699 (2019).Article
CAS
Google Scholar
Lightburn, T. E., Dombrowski, M. T. & Tan, K. L. Catalytic scaffolding ligands an efficient strategy for directing reactions. J. Am. Chem. Soc. 130, 9210–9211 (2008).Article
CAS
PubMed
Google Scholar
Breit, B. & Zahn, S. K. Domino hydroformylation-wittig reactions. Angew. Chem. Int. Ed. 38, 969–971 (1999).Article
CAS
Google Scholar
Wong, G. W. & Landis, C. R. Iterative asymmetric hydroformylation/Wittig olefination sequence. Angew. Chem. Int. Ed. 52, 1564–1567 (2013).Article
CAS
Google Scholar
Watkins, A. L. & Landis, C. R. Origin of Pressure Effects on Regioselectivity and Enantioselectivity in the Rhodium-Catalyzed Hydroformylation of Styrene with (S,S,S)-BisDiazaphos. J. Am. Chem. Soc. 132, 10306–10317 (2010).Article
CAS
PubMed
Google Scholar
Brezny, A. C. & Landis, C. R. Unexpected CO dependencies, catalyst speciation, and single turnover hydrogenolysis studies of hydroformylation via high pressure NMR spectroscopy. J. Am. Chem. Soc. 139, 2778–2785 (2017).Article
CAS
PubMed
Google Scholar
Xu, K., Zheng, X., Wang, Z. & Zhang, X. Easily accessible and highly tunable bisphosphine ligands for asymmetric hydroformylation of terminal and internal alkenes. Chem. Eur. J. 20, 4357–4362 (2014).Article
CAS
PubMed
Google Scholar
Aguado-Ullate, S., Guasch, L., Urbano-Cuadrado, M., Bo, C. & Carbo, J. J. 3D-QSPR models for predicting the enantioselectivity and the activity for asymmetric hydroformylation of styrene catalyzed by Rh−diphosphane. Catal. Sci. Technol. 2, 1694–1704 (2012).Article
CAS
Google Scholar
Phanopoulos, A. & Nozaki, K. Branched-selective hydroformylation of nonactivated olefins using an n-triphos/rh catalyst. ACS Catal. 8, 5799–5809 (2018).Article
CAS
Google Scholar
Bickelhaupt, F. M. & Houk, K. N. Analyzing reaction rates with the distor-tion/interaction-activation strain model. Angew. Chem., Int. Ed. 56, 10070–10086 (2017).Article
CAS
Google Scholar
Johnson, E. R. et al. Revealing noncovalent interactions. J. Am. Chem. Soc. 132, 6498–6506 (2010).Article
CAS
PubMed
PubMed Central
Google Scholar
Bader, R. F. W. A quantum theory of molecular structure and its applications. Chem. Rev. 91, 893–928 (1991).Article
CAS
Google Scholar
Parthasarathi, R., Subramanian, V. & Sathyamurthy, N. Hydrogen bonding without borders: an atoms-in-molecules perspective. J. Phys. Chem. A. 110, 3349–3351 (2006).Article
CAS
PubMed
Google Scholar
Prakash, M., Samy, G. K. & Subramanian, V. Benzene−Water (BZWn (n = 1 − 10)) Clusters. J. Phys. Chem. A. 113, 13845–13852 (2009).Article
CAS
PubMed
Google Scholar
Danovich, D. et al. Understanding the Nature of the CH···HC Interactions in Alkanes. J. Chem. Theory Comput. 9, 1977–1991 (2013).Article
CAS
PubMed
Google Scholar
Singh, S. & Sunoj, R. B. Chapter One – Computational asymmetric catalysis: On the origin of stereoselectivity in catalytic reactions. Adv. Phys. Org. Chem. (eds. Williams, I. H. & Williams, N. H.) 53, 1–27 (2019).