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
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).
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.
