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Copper-Catalyzed Enantioselective Synthesis of Axially Chiral Allenes

Hailing Li, Daniel Müller, Laure Guénée and Alexandre Alexakis*

*Department of Organic Chemistry, University of Geneva 30, and Laboratory of Crystallography, University of Geneva 24, quai Ernest Ansermet CH-1211 Geneva 4, Switzerland, Email:

H. Li, D. Müller, L. Guénée, A. Alexakis, Org. Lett., 2012, 14, 5880-5883.

DOI: 10.1021/ol302790e (free Supporting Information)

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A simple copper-catalyzed enantioselective synthesis of axially chiral chloroallenes from propargylic dichlorides leads to exclusive formation of the desired allenes with good enantioselectivities. Further transformations to trisubstituted allenes or terminal alkynes with a propargylic quaternary carbon center keep a high level of enantiopurity.

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ID: J54-Y2012-3720