Published October 19, 2012
| Accepted Version + Supplemental Material
Journal Article
Open
Lewis Acid Mediated (3 + 2) Cycloadditions of Donor–Acceptor Cyclopropanes with Heterocumulenes
Chicago
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Abstract
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
Files
nihms413989.pdf
Additional details
- PMCID
- PMC3490221
- Eprint ID
- 35762
- Resolver ID
- CaltechAUTHORS:20121203-103554504
- NIH
- R01GM080269-01
- Amgen
- Abbott
- Boehringer-Ingelheim
- Caltech
- Natural Sciences and Engineering Research Council of Canada (NSERC)
- NSF
- CHE-0639094
- NIH
- RR027690
- Created
-
2012-12-05Created from EPrint's datestamp field
- Updated
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2023-03-16Created from EPrint's last_modified field