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Org Lett. 2012 Dec 7;14(23):5880-3. doi: 10.1021/ol302790e. Epub 2012 Nov 12.

Copper-catalyzed enantioselective synthesis of axially chiral allenes.

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  • 1Department of Organic Chemistry, University of Geneva 30, quai Ernest Ansermet CH-1211 Geneva 4, Switzerland.


A simple copper-catalyzed enantioselective synthesis of axially chiral chloroallenes from the propargylic dichlorides is reported, employing a catalytic amount of easily prepared SimplePhos ligand. Exclusive formation of the desired allenes was observed with good enantioselectivities (ee's 62-96%). Further transformations to trisubstituted allenes or terminal alkynes with a propargylic quaternary carbon center keep a high level of enantiopurity.

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