Synfacts 2010(1): 0078-0078  
DOI: 10.1055/s-0029-1218512
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart ˙ New York

Rhodium-Catalyzed Asymmetric Conjugate Alkynylation

Contributor(s): Hisashi Yamamoto, Dmitry L. Usanov
T. Nishimura*, T. Sawano, T. Hayashi*
Kyoto University, Japan
Further Information

Publication History

Publication Date:
21 December 2009 (online)

Significance

The asymmetric conjugate addition of alkynes to an α,β-unsaturated system is an atom-economical synthetic approach which allows the formation of a chiral carbon center in the propargylic position. However, the catalytic asymmetric 1,4-alkynylation of enals has been unknown so far. In this paper, the authors report the first example of this transformation via catalysis by a rhodium complex of chiral DTBM-segphos, which proceeds with high yields and excellent enantioselectivities.