anti-Selective Michael Reaction of Aldehydes

Significance

The authors report highly anti-­selective Michael reactions of TBS-protected ­hydroxyacetaldehyde (1) with nitroolefins 2 catalyzed by a thiourea catalyst 3 bearing a primary amine function. The reaction was efficient with electron-rich, electron-deficient, and sterically hindered nitrostyrenes as well as alkyl-substituted ­nitroolefins and yielded the corresponding Michael adducts 4 in excellent diastereoselectivity and enantioselectivity.