Dill, J. D., Greenberg, A. & Liebman, J. F. Substituent effects on strain energies. J. Am. Chem. Soc. 101, 6814–6826 (1979).
De Meijere, A. Bonding properties of cyclopropane and their chemical consequences. Angew. Chem. Int. Ed. 18, 809–886 (1979). This useful report details many properties and reactivity trends of cyclopropanes.
Chen, D. Y.-K., Pouwer, R. H. & Richard, J.-A. Recent advances in the total synthesis of cyclopropane-containing natural products. Chem. Soc. Rev. 41, 4631–4642 (2012).
Article CAS PubMed Google Scholar
Fan, Y.-Y., Gao, X.-H. & Yue, J.-M. Attractive natural products with strained cyclopropane and/or cyclobutane ring systems. Sci. China Chem. 59, 1126–1141 (2016).
Ma, S., Mandalapu, D., Wang, S. & Zhang, Q. Biosynthesis of cyclopropane in natural products. Nat. Prod. Rep. 39, 926–945 (2022).
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). This Perspective outlines contemporary pharmaceuticals and pharmaceutical candidates that contain a cyclopropane, as well as the contributions of a cyclopropyl ring to the properties of these drugs.
Article CAS PubMed Google Scholar
Časar, Z. Synthetic approaches to contemporary drugs that contain the cyclopropyl moiety. Synthesis 52, 1315–1345 (2020).
Ebner, C. & Carreira, E. M. Cyclopropanation strategies in recent total syntheses. Chem. Rev. 117, 11651–11679 (2017).
Article CAS PubMed Google Scholar
Sansinenea, E. & Ortiz, A. The chemistry of cyclopropanes and new insights into organocatalyzed asymmetric cyclopropanation. Eur. J. Org. Chem. 2022, e202200210 (2022).
Bartoli, G., Bencivenni, G. & Dalpozzo, R. Asymmetric cyclopropanation reactions. Synthesis 46, 979–1029 (2014).
Wenbing, J., Hua, Y. & Gongli, T. Strategies for construction of cyclopropanes in natural products. China J. Org. Chem. 38, 2324–2334 (2018).
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
Jana, R., Pathak, T. P. & Sigman, M. S. Advances in transition metal (Pd, Ni, Fe)-catalyzed cross-coupling reactions using alkyl-organometallics as reaction partners. Chem. Rev. 111, 1417–1492 (2011).
Article CAS PubMed PubMed Central Google Scholar
De Meijere, A. & Diederich, F. Metal-Catalyzed Cross-Coupling Reactions 2nd edn, Vol. 1 (Wiley-VCH, 2004).
De Meijere, A. & Diederich, F. Metal-Catalyzed Cross-Coupling Reactions 2nd edn, Vol. 2 (Wiley-VCH, 2004).
Rubin, M., Rubina, M. & Gevorgyan, V. Transition metal chemistry of cyclopropenes and cyclopropanes. Chem. Rev. 107, 3117–3179 (2007). This comprehensive review contains a thorough overview of early cross-coupling reactions at cyclopropane up to 2007 (that is, Suzuki, Kumada, Negishi, Stille and C–H activation).
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
Blanksby, S. J. & Ellison, G. B. Bond dissociation energies of organic molecules. Acc. Chem. Res. 36, 255–263 (2003).
Article CAS PubMed Google Scholar
Pirenne, V., Muriel, B. & Waser, J. Catalytic enantioselective ring-opening reactions of cyclopropanes. Chem. Rev. 121, 227–263 (2021).
Article CAS PubMed Google Scholar
Wang, L. J. & Tang, Y. Asymmetric ring-opening reactions of donor–acceptor cyclopropanes and cyclobutanes. Isr. J. Chem. 56, 463–475 (2016).
Quan, L. G., Lee, H. G. & Cha, J. K. Acid- and Pd(0)-catalyzed ring opening of 1-(1-cycloalkenyl)cyclopropyl sulfonates. Org. Lett. 9, 4439–4442 (2007).
Article CAS PubMed Google Scholar
Sarel, B. S., Yovell, J. & Sarel-Imber, M. Recent developments in the stereochemistry of cyclopropane ring opening. Angew. Chem. Int. Ed. 7, 577–588 (1968).
DePuy, C. H. The chemistry of cyclopropanols. Acc. Chem. Res. 1, 33–41 (1968).
Schleyer, P. V. R., Su, T. M., Saunder, M. & Rosenfield, J. C. The stereochemistry of allyl cations from the isomeric 2,3-dimethylcyclopropyl chlorides. The stereomutation of allyl cations. J. Am. Chem. Soc. 91, 5174–5176 (1969).
Marek, I., Masarwa, A., Delaye, P.-O. & Leibeling, M. Selective carbon–carbon cleavage for the stereoselective synthesis of acyclic systems. Angew. Chem. Int. Ed. 54, 414–429 (2015).
Miyaura, N. in Metal-Catalyzed Cross-Coupling Reactions (eds de Meijere, A. & Diederich, F.) 41–124 (Wiley-VCH, 2004).
Wang, X.-Z. & Deng, M.-Z. Cross-coupling reaction of cyclopropylboronic acid with bromoarenes. J. Chem. Soc. Perkin Trans. 1, 2663–2664 (1996).
Ma, H.-R., Wang, X.-H. & Deng, M.-Z. Palladium-catalyzed cross-coupling reaction of stereodefined cyclopropylboronic acids with N-heterocycle bromides. Synth. Commun. 29, 2477–2485 (1999).
Yao, M.-L. & Deng, M.-Z. A practical approach to stereodefined cyclopropyl-substituted heteroarenes using a Suzuki-type reaction. N. J. Chem. 24, 425–428 (2000).
Yao, M.-L. & Deng, M.-Z. Palladium-catalyzed cross-coupling reaction of cyclopropylboronic acids with aryl triflates. Synthesis 8, 1095–1100 (2000).
Zhou, A.-M., Deng, M.-Z., Xia, L.-J. & Tang, M.-H. Efficient Suzuki-type cross-coupling of enantiomerically pure cyclopropylboronic acids. Angew. Chem. Int. Ed. 37, 2845–2847 (1998).
Rubina, M., Rubin, M. & Gevorgyan, V. Catalytic enantioselective hydroboration of cyclopropenes. J. Am. Chem. Soc. 125, 7198–7199 (2003).
Article CAS PubMed Google Scholar
Wallace, D. J. & Chen, C.-Y. Cyclopropylboronic acid: synthesis and Suzuki cross-coupling reactions. Tetrahedron Lett. 43, 6987–6990 (2002).
Lemhadri, M., Doucet, H. & Santelli, M. Suzuki coupling of cyclopropylboronic acid with aryl halides catalyzed by a palladium–tetraphosphine complex. Synth. Commun. 36, 121–128 (2006).
Zhang, W. et al. Facile synthesis of aryl(het)cyclopropane catalyzed by palladacycle. Tetrahedron 68, 900–905 (2012).
Zhou, S.-M., Yan, Y.-L. & Deng, M.-Z. A novel stereocontrolled synthesis of cyclopropyl-substituted α, β-unsaturated esters: palladium catalyzed cross-coupling of cyclopropylboronic acids with bromoacrylates. Synlett 2, 198–200 (1998).
Yao, M.-L. & Deng, M.-Z. Facile approach to 4-substituted 2(5H)-furanones. J. Org. Chem. 65, 5034–5036 (2000).
Article CAS PubMed Google Scholar
Yao, M.-L. & Deng, M.-Z. Palladium-catalyzed cross-coupling of cyclopropylboronic acids with alkenyl triflates. Tetrahedron Lett. 41, 9083–9087 (2000).
Chen, H. & Deng, M.-Z. A novel stereocontrolled synthesis of 1,2-trans cyclopropyl ketones via Suzuki-type coupling of acid chlorides with cyclopropylboronic acids. Org. Lett. 2, 1649–1651 (2000).
Article CAS PubMed Google Scholar
Chen, H. & Deng, M.-Z. Silver oxide mediated palladium-catalyzed cross-coupling reaction of cyclopropylboronic acids with allylic bromides. J. Org. Chem. 65, 4444–4446 (2000).
Article CAS PubMed Google Scholar
Lennox, A. J. J. & Lloyd-Jones, G. C. Selection of boron reagents for Suzuki–Miyaura coupling. Chem. Soc. Rev. 43, 412–443 (2014).
Article CAS PubMed Google Scholar
Hildebrand, J. P. & Marsden, S. P. A novel, stereocontrolled synthesis of 1,2-trans-cyclopropanes: cyclopropyl boronate esters as partners in Suzuki couplings with aryl halides. Synlett 9, 893–894 (1996). This is the first report of Suzuki coupling at a cyclopropane.
Chen, H. & Deng, M.-Z. A novel Suzuki-type cross-coupling reaction of cyclopropylboronic esters with benzyl bromides. J. Chem. Soc. Perkin Trans. 1, 1609–1613 (2000).
Charette, A. B. & De Freitas-Gil, R. Synthesis of contiguous cyclopropanes by palladium-catalyzed Suzuki-type cross-coupling reactions. Tetrahedron Lett. 38, 2809–2812 (1997).
Peitruszka, J., Witt, A. & Frey, W. Synthesis of ‘Garner’ aldehyde-derived cyclopropylboronic esters. Eur. J. Org. Chem. 2003, 3219–3229 (2003).
Löhr, S. & de Meijere, A. 2-(Bicyclopropylidenyl)- and 2-(trans−2’-
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