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Synfacts 2008(3): 0281-0281  
DOI: 10.1055/s-2008-1042704
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York

Stereoselective Synthesis of α-Substituted Z-Homoallylic Alcohols

Contributor(s): Mark Lautens, Frédéric Ménard
Y. Sato*, Y. Hinata, R. Seki, Y. Oonishi, N. Saito
Hokkaido University, Sapporo, Japan
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Publication History

Publication Date:
21 February 2008 (online)

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Significance

The use of chiral N-heterocyclic carbenes (NHC) in synthesis is increasing rapidly as more classes of reactions are developed. Taking advantage of the strong affinity of nickel(0) for NHCs, the Sato group developed a stereoselective reductive coupling reaction between dienes and aldehydes. The enantioselectivity with chiral NHCs is still in need of improvement as reactions with >90% ee are still rare. The catalytic system above therefore represents a significant step forward.