Aldol Additions to Aldehydes with an Indathiazolidinethione Auxiliary

Significance

Diastereoselective acetate-type aldol reactions have generally been more challenging than the extensively studied analogous propionate-type aldol. The titanium-mediated aldol reaction with a range of aldehydes gave the chiral adducts 3 with diastereoselectivity comparable to other existing methods. However, the present method is advantageous in terms of cost and preparation of the chiral auxiliary. The chiral auxiliary was prepared in two steps from trans-1-amino-2-hydroxyindane, of which both enantiomers are commercially available.