Double diastereoselective acetate aldol reactions with chiral N-acetyl thiazolidinethione reagents.
Double diastereoselective acetate aldol reactions using the N-acetyl thiazolidinethione-based chiral auxiliaries 1 and 2 and chiral aldehydes are described. Aldehydes that bear alpha-alkyl stereocenters exhibit moderate levels of double diastereoselection, while those that bear alpha- or beta-alkoxy substitution exhibit little to no double diastereoselection. In all cases studied, the stereoselectivity of the reaction is dictated by the reagent, not the substrate.
Zhang
Yingchao
Y
Department of Chemistry and Biochemistry, University of Colorado, Boulder, Colorado 80309-0215, USA.
Sammakia
Tarek
T
D000085:Acetates / Q000737:chemistry*; D000447:Aldehydes / Q000737:chemistry*; D006865:Hydrogenation; D007097:Imines / Q000737:chemistry; D015394:Molecular Structure; D013237:Stereoisomerism; D053778:Thiazolidines / Q000737:chemistry*
D000085:Acetates; D000447:Aldehydes; D007097:Imines; D053778:Thiazolidines; C033089:thiazoline-2-thione; C116609:3-hydroxybutanal