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H. Li, D. Müller, L. Guénée, A. Alexakis,
“Copper-Catalyzed Enantioselective Synthesis of Axially Chiral Allenes”
Org. Lett. 2012, 14, 5880-5883.
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.
DOI : 10.1021/ol302790e
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