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Published June 2016 | Accepted Version
Journal Article Open

Synthetic Applications and Methodological Developments of Donor-Acceptor Cyclopropanes and Related Compounds


Donor-acceptor cyclopropanes are convenient precursors to reactive and versatile 1,3-dipoles, and have found application in the synthesis of a variety of carbo- and heterocyclic scaffolds. This perspective review details our laboratory's use of donor-acceptor cyclopropanes as intermediates toward the total synthesis of various natural products. We also discuss our work in the development of novel cycloadditions and rearrangements of donor-acceptor cyclopropanes and aziridines, as well as an example of an aryne insertion proceeding via fragmentation of a transient donor-acceptor cyclobutane.

Additional Information

© 2016 Wiley-VCH Verlag GmbH &Co. KGaA, Weinheim. Received: November 9, 2015; Accepted: December 7, 2015; Article first published online: 27 Jan. 2016. The authors thank the coworkers whose efforts have made our contributions to the chemistry of donor-acceptor cyclopropanes and related compounds possible: Jennifer M. Chen, Robert A. Craig, II, Hans-Jürgen Dietrich, Julie A. Dixon, Brian D. Doan, John A. Enquist, Jr., Eric M. Ferreira, Alexander F. G. Goldberg, Timothy P. Heffron, Alexandra A. Holubec, Michael E. Meyer, Dejah T. Petsch, Derek A. Pflum, John H. Phillips, Richmond Sarpong, Mohammed F. Shamji, Grant M. Shibuya, Julius T. Su, Uttam K. Tambar, and Matthew M. Weiss. Financial support from the A. P. Sloan Foundation, Abbott, the American Cancer Society (JFRA-523), Amgen, Astellas Pharma, AstraZeneca, Bayer Corporation, Boehringer Ingelheim, Bristol-Myers Squibb, Caltech, the Camille and Henry Dreyfus Foundation, Eli Lilly, the Elsa U. Pardee Foundation, GlaxoSmithKline, Johnson & Johnson, Merck, the NIH-NIGMS (R01GM080269), Novartis, the NSF CCI Center for Selective C-H Functionalization (CHE-1205646), Pfizer, the Research Corporation, Roche, and Yale University is gratefully acknowledged. J.L.W. is grateful for generous funding from Baylor University, the Welch Foundation (Chair, AA-006), and the Cancer Prevention & Research Institute of Texas (CPRIT, R1309).

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