Synfacts 2010(7): 0803-0803  
DOI: 10.1055/s-0029-1220084
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart ˙ New York

Asymmetric Addition of 1,3-Diynes to Aldehydes

Contributor(s): Mark Lautens, David A. Candito
B. M. Trost*, V. S. Chan, D. Yamamoto
Stanford University, USA
Further Information

Publication History

Publication Date:
22 June 2010 (online)

Significance

Diyne carbinols are structural elements commonly found in fatty acid derived polyacetylenic natural products. The most common strategy in the preparation of these natural products relies on asymmetric reduction of an ynone followed by Cadiot-Chodkiewicz cross-coupling. The authors report on the ProPhenol-catalyzed asymmetric addition of 1,3-diynes to aldehydes. This strategy allows for the creation of stereo­chemistry and C-C bond formation to take place in one operation. This report represents the first efficient asymmetric addition of a 1,3-diyne to an aldehyde. The authors go on to demonstrate the power of this methodology in the synthesis of several natural products.