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Synfacts 2010(5): 0561-0561  
DOI: 10.1055/s-0029-1219704
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart ˙ New York

Indium(I)-Catalyzed Allylation and Crotylation of Imines

Contributor(s): Mark Lautens, Jane Panteleev
A. Chakrabarti, H. Konishi, M. Yamaguchi, U. Schneider, S. Kobayashi*
The University of Tokyo, Japan
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Publikationsdatum:
22. April 2010 (online)

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Significance

The authors report indium-catalyzed allylation, chloroallylation, and crotylation of hydrazones. Although asymmetric allylations are well established, this work is an improvement in addition to less reactive imines. While indium(III) is often used as a Lewis acid, the utilization of indium(I) complexes in catalytic amounts is less common. This well-behaved reaction affords homo­allylic hydrazines in great yields and reportedly higher enantioselectivity than previously observed.