Asymmetric Addition of 1,3-Diynes to Aldehydes

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.