Organic Chemistry Portal



Enantioselective organocatalytic aldehyde-aldehyde cross-aldol couplings. The broad utility of α-thioacetal aldehydes

R. Ian Storer and David W. C. MacMillan*

*Division of Chemistry and Chemical Engineering, California Institute of Technology, 1200 E California Blvd;, Pasadena, CA 91125, USA, Email:

R. I. Storer, D. W. C. MacMillan, Tetrahedron, 2004, 60, 7705-7714.

DOI: 10.1016/j.tet.2004.04.089


An asymmetric proline catalyzed cross-aldol reaction with α-thioacetal aldehydes as electrophilic partners has been developed. Anti-aldol adducts are produced with high levels of reaction efficiency as well as diastereo- and enantiocontrol with a broad range of aldehyde and ketone donors.

see article for more examples

Key Words

Aldol, Catalysis, Diastereoselection, Enantioselective, Organocatalysis, Proline, Aldol Addition

ID: J72-Y2004-670