Activated Cyclopropanes: A Remarkable Breadth of Recent Chemistry

Abstract

The reactions of cyclopropanes activated by electron-withdrawing groups and electron-donating groups – donor–acceptor (DA) cyclopropanes – and with alkenyl or alkylidene substituents has been an area of recent intense research activity. This Cluster contains contributions from many of the leading research groups in this area, and provides a concise introduction to the rich ring-opening, ring-expansion, dimerization, and cycloaddition chemistry of these compounds.

Key words

cyclopropanes - ring opening - cycloaddition - rearrangement - Lewis acids - catalysis

• References

• 1 de Meijere A. Angew. Chem., Int. Ed. Engl. 1979; 18: 809
• 2a Donaldson WA. Tetrahedron 2000; 56: 8589
• 2b Faust R. Angew. Chem. Int. Ed. 2001; 40: 2251
• 2c Chen DY.-K, Pouwer RH, Richard J.-A. Chem. Soc. Rev. 2012; 41: 4631
• 3a Lebel H, Marcoux J.-F, Molinaro C, Charette AB. Chem. Rev. 2003; 103: 977
• 3b Pellissier H. Tetrahedron 2008; 64: 7041
• 4a Charette AB, Beauchemin A. Org. React. 2001; 58: 1
• 4b Concellón JM, Rodríguez-Solla H, Concellón C, del Amo V. Chem. Soc. Rev. 2010; 39: 4130
• 5 Fedoryński M. Chem. Rev. 2003; 103: 1099
• 6a Doyle MP. J. Org. Chem. 2006; 71: 9253
• 6b Wee AG. Curr. Org. Synth. 2006; 3: 499
• 7 Cha JK, Kulinkovich OG. Org. React. 2012; 77: 1
• 8 Wiberg KB. Angew. Chem., Int. Ed. Engl. 1986; 25: 312
• 9 For early work on acceptor-substituted cyclopropanes, see: Danishefksy S. Acc. Chem. Res. 1979; 12: 66

For early work on donor-substituted cyclopropanes, see:
• 10a Saluan JR. Y. Top. Curr. Chem. 1988; 144: 1
• 10b Kuwajima I, Nakamura E. Top. Curr. Chem. 1990; 155: 1
• 10c Kulinkovich OG. Chem. Rev. 2003; 103: 1071
• 11 For early work on donor–acceptor cyclopropanes, see: Reissig H.-U, Zimmer R. Chem. Rev. 2003; 103: 1151

For reviews on multiple facets of earlier cyclopropane chemistry, see:
• 12a Wong HN. C, Hon MY, Tse CW, Yip YC, Tanko J, Hudlicky T. Chem. Rev. 1989; 89: 165
• 12b Rubin M, Rubina M, Gevorgyan V. Chem. Rev. 2007; 107: 3117
• 12c Tang P, Gin Y. Synthesis 2012; 44: 2969
• 13a Yu M, Pagenkopf BL. Tetrahedron 2005; 61: 321
• 13b Carson CA, Kerr MA. Chem. Soc. Rev. 2009; 38: 2969
• 13c Campbell MJ, Johnson JS, Parson AT, Pohlhaus PD, Sanders SD. J. Org. Chem. 2010; 75: 6317
• 13d Lebold TP, Kerr MA. Pure Appl. Chem. 2010; 82: 1797
• 13e Mel’nikov MYa, Budynina EM, Ivanova OA, Trushkov IV. Mendeleev Commun. 2011; 21: 293
• 13f Tang P, Qin Y. Synthesis 2012; 44: 2311
• 13g Wang Z. Synlett 2012; 23: 2311
• 13h Schneider TF, Kaschel J, Werz DB. Angew. Chem. Int. Ed. 2014; 53: 5504
• 13i de Nanteuil F, De Simone F, Frei R, Benfatti F, Serrano E, Waser J. Chem. Commun. 2014; 50: 10912
• 14a Masarwa A, Marek I. Chem. Eur. J. 2010; 16: 9712
• 14b Pellissier H. Tetrahedron 2010; 66: 8341
• 14c Zhang D.-H, Tang X.-Y, Shi M. Acc. Chem. Res. 2014; 913
• 14d Brandi A, Cicchi S, Cordero FM, Goti A. Chem. Rev. 2014; 114: 7317
• 14e Mack DJ, Njardson JT. ACS Catal. 2013; 3: 272
• 15 Jiao L, Yu Z.-X. J. Org. Chem. 2013; 78: 6842