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

Müller, Daniel
Mauduit, Marc
Published in Organic Letters. 2011, vol. 13, no. 6, p. 1524 - 1527
Abstract 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.
Stable URL https://archive-ouverte.unige.ch/unige:14606
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Other version: http://pubs.acs.org/doi/abs/10.1021/ol200219m

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Deposited on : 2011-03-14

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