Highly Enantioselective and Regioselective Copper-Catalyzed 1,4 Addition of Grignard Reagents to Cyclic Enynones

In this letter we describe an unusual result in terms of regioselectivity with respect to copper-catalyzed conjugate additions of various Grignard reagents to cyclic enynones. The use of Cu(OTf)2 and NHC ligand L1 as the catalyst combination in CH2Cl2 led to the unique formation of the 1,4 adduct. T...

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Bibliographic Details
Published in:Organic letters 2011-03, Vol.13 (6), p.1524-1527
Main Authors: Tissot, Matthieu, Pérez Hernández, Alexandra, Müller, Daniel, Mauduit, Marc, Alexakis, Alexandre
Format: Article
Language:English
Subjects:
Chemical Sciences
Organic chemistry
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Summary:In this letter we describe an unusual result in terms of regioselectivity with respect to copper-catalyzed conjugate additions of various Grignard reagents to cyclic enynones. The use of Cu(OTf)2 and NHC ligand L1 as the catalyst combination in CH2Cl2 led to the unique formation of the 1,4 adduct. This selectivity does not follow the general trend previously observed in the literature using extended Michael acceptors. Moreover these reactions allowed for the creation of a quarternary stereogenic center with enantioselectivities up to 97% ee.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol200219m