Journal
TETRAHEDRON
Volume 67, Issue 24, Pages 4313-4317Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2011.04.029
Keywords
Asymmetric cyclopropenation; Cyclopropenes; Donor/acceptor carbenoids; Dirhodium catalysis; Siloxyvinyldiazoacetate
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Funding
- National Science Foundation [CHE-0750273]
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Rh-2(S-PTAD)(4) is an effective catalyst for the asymmetric cyclopropenation of aryl alkynes using a siloxyvinyldiazoacetate as the carbenoid precursor. Upon deprotection of the silyl protecting group, highly enantioenriched cyclopropenes bearing geminal acceptor groups can be accessed. These cyclopropenes undergo regioselective rhodium(II)-catalyzed ring expansion to furans. (C) 2011 Elsevier Ltd. All rights reserved.
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