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Synfacts 2014; 10(11): 1175
DOI: 10.1055/s-0034-1379323
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York

Enantioselective Allyl–Allylsilane Cross-Coupling Catalyzed by Iridium

Contributor(s):
Hisashi Yamamoto
,
Masahiro Sai
Hamilton JY, Hauser N, Sarlah D, Carreira EM * ETH Zürich, Switzerland
Iridium-Catalyzed Enantioselective Allyl–Allylsilane Cross-Coupling.

Angew. Chem. Int. Ed. 2014;
53: 10759-10762
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Further Information

Publication History

Publication Date:
20 October 2014 (online)

 
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Key words

allylsilanes - cross-coupling - iridium

Significance

An iridium-catalyzed cross-coupling of allylic alcohols with allylsilanes is reported. A series of chiral 1,5-dienes were prepared in good yields (up to 95%) with excellent regio- (up to >25:1) and enantioselectivities (up to >99% ee).


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Comment

This allyl–allylsilane cross-coupling proceeds with excellent regio- and enantioselectivity under operationally simple conditions. The utility of this reaction is demonstrated in the enantioselective synthesis of the pyrethroid insecticide protrifenbute.


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