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Synfacts 2007(11): 1182-1182  
DOI: 10.1055/s-2007-991247
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York

Gold-Catalyzed Synthesis of Cyclohexenediol Derivatives

Contributor(s): Mark Lautens, Frédéric Ménard
C. Lim, J.-E. Kang, J.-E. Lee, S. Shin*
Hanyang University and Gyeongsang National University, Chinju, Korea
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Publication History

Publication Date:
23 October 2007 (online)

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Significance

Gold(I) complexes were shown to be effective catalysts for the cyclization of 1,5-enynes. A cationic intermediate, 3, was trapped with an intramolecular carbonate as oxygen source. This reaction allows a rapid increase in molecular complexity from readily available substrates 1, which are prepared by coupling propargylic Grignard reagents with α,β-unsaturated aldehydes. Up to three contiguous stereocenters can be set with high selectivity.