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Synfacts 2008(1): 0069-0069  
DOI: 10.1055/s-2007-991482
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York

Enantioselective Allylation Catalyzed by Indium Complexes

Contributor(s): Mark Lautens, Michael Langer
K. Zheng, B. Qin, X. Liu, X. Feng*
Sichuan University, Chengdu, P. R. of China
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Publication History

Publication Date:
18 December 2007 (online)

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Significance

Optically active α-hydroxy acids can be found in pharmaceutical agents and natural products. The authors present a mild method for the synthesis of enantioenriched α ,α-allyl hydroxyl esters by enantioselective allylation of α-keto esters with tetraallylstannane in the presence of a chiral indium(III) catalyst. The method can be carried out under very mild conditions and is tolerant towards air and moisture. For previous work on cyanation and allylation by the same group, see: Tetrahedron Lett. 2006, 47, 4011; J. Org. Chem. 2007, 72, 5227.