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Published October 19, 2012 | Accepted Version + Supplemental Material
Journal Article Open

Lewis Acid Mediated (3 + 2) Cycloadditions of Donor–Acceptor Cyclopropanes with Heterocumulenes


Isocyanates, isothiocyanates, and carbodiimides are effective substrates in (3 + 2) cycloadditions with donor–acceptor cyclopropanes for the synthesis of five-membered heterocycles. These reactions exhibit a broad substrate scope, high yields, and well-defined chemoselectivity. Discussed herein are the implications of Lewis acid choice on the stereochemical outcome and the reaction mechanism.

Additional Information

© 2012 American Chemical Society. Publication Date (Web): October 9, 2012. The authors wish to thank NIH-NIGMS (R01GM080269-01), Amgen, Abbott, Boehringer Ingelheim, and Caltech for financial support. A.G. gratefully acknowledges the Natural Sciences and Engineering Research Council (NSERC) of Canada for a PGS D scholarship. Dr. Michael R. Krout (Bucknell University) and Jonathan R. Gordon (Caltech) are thanked for helpful discussions. Lawrence Henling (Caltech) is gratefully acknowledged for X-ray crystallographic structural determination. The Bruker KAPPA APEXII X-ray diffractometer was purchased via an NSF CRIF:MU award to the California Institute of Technology, CHE-0639094. The Varian 400 MHz NMR spectrometer was purchased via an NIH grant (RR027690).

Attached Files

Accepted Version - nihms413989.pdf

Supplemental Material - ol302494n_si_001.pdf

Supplemental Material - ol302494n_si_002.cif

Supplemental Material - ol302494n_si_003.cif


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August 19, 2023
October 20, 2023