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Synfacts 2006(3): 0238-0238
DOI: 10.1055/s-2006-931948
DOI: 10.1055/s-2006-931948
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York
Asymmetric Intramolecular Cyclopropanation towards Fused Cyclopropyllactones
W. Lin, A. B. Charette*
Université de Montréal, Canada
Further Information
Publication History
Publication Date:
21 February 2006 (online)
Significance
Asymmetric intermolecular cyclopropanations are well documented; however, highly enantioselective intramolecular examples are less common. This report describes a method for intramolecular cyclopropanation using a carbenoid precursor flanked on both sides by electron-withdrawing groups. Yields and enantioselectivities vary widely and demonstrate the difficulty of this reaction. Interestingly, vinyl halides are tolerated and allow for the enantioselective synthesis of halocyclopropanes.