Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 55, Issue 23, Pages 6780-6783Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201601340
Keywords
cycloaddition; cyclopropane; donor-acceptor systems; oxocarbenium ions; tetrahydrofuran
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Funding
- University of Vienna
- Deutsche Forschungsgemeinschaft [MA 4861/3-1]
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A novel formal [3 + 2] cycloaddition of cyclopro-pylacetals and aldehydes was developed, and the resulting trisubstituted tetrahydrofurans display three new chiral centers formed with highly diastereoselectivity. This method is stereo-complementary to most previously reported cycloadditions of malonate diesters, relies on the transient generation of cyclopropyl oxocarbenium ions, proceeds under mild conditions, and is based on the concept of temporary activation of an otherwise inert protecting group.
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