Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 131, Issue 22, Pages 7536-+Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ja902137z
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A new method for cyclopropanation involving intramolecular methylene transfer from an epoxide to an olefin has been developed. This La(OTf)(3)-catalyzed process proceeds with good efficiency and with high stereoselectivity. A range of examples illustrating substrate scope are given along with a mechanistic rationale. Also demonstrated is an asymmetric cyclopropane synthesis that combines enantioselective epoxidation with this methylene-transfer protocol.
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