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

Article Article scientifique Article Highly Enantioselective and Regioselective Copper-Catalyzed 1,4 Addition of Grignard Reagents to Cyclic Enynones eng 2011 author Tissot Matthieu 133733 author Perez Hernandez Alexandra 633046 author Müller Daniel author Mauduit Marc author Alexakis Alexandre 123950 1524-1527 10.1021/ol200219m 1523-7052 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. Dewey 540 36 Département de chimie organique 141 false Organic letters 13 6 21fed440-b152-47fa-8fe8-0bbd8dd6fb77 Article (Published version) Restricted ol200219m.pdf 710486 application/pdf Private 2012-03-14 restrictedAccess Faculté des sciences / Section de chimie et biochimie / Département de chimie organique

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Highly Enantioselective and Regioselective Copper-Catalyzed 1,4 Addition of Grignard Reagents to Cyclic Enynones	Organic letters			2011	620	0

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Perez Hernandez, Alexandra