Synfacts 2019; 15(01): 0083
DOI: 10.1055/s-0037-1611404
Organo- and Biocatalysis
© Georg Thieme Verlag Stuttgart · New York

Chiral Lewis Base Catalyzed Aldol Reaction of Unprotected Carboxylic Acids

Benjamin List
Vikas Kumar Singh
Yoshiwara Y, Ogasawara M, Sugiura M, Kotani S. * Nakajim M. Kumamoto University, Tokushima University, and Sojo University, Kumamoto, Japan
Catalytic Enantioselective Aldol Reaction of Unprotected Carboxylic Acids under Phosphine Oxide Catalysis.

Angew. Chem. Int. Ed. 2018;
57: 15877-15881
Further Information

Publication History

Publication Date:
14 December 2018 (online)



Nakajima and co-workers report the first example of a chiral Lewis base-catalyzed ­SiCl4-mediated enantioselective aldol reaction of unprotected carboxylic acids. The method is highly enantio- and diastereoselective, and it shows a broad substrate scope.



Previous works on asymmetric aldol reactions of unprotected carboxylic acids by various groups (see, for example: K. Yu et al. J. Am. Chem. Soc. 2017, 139, 527) required stoichiometric chiral reagents to achieve enantioselectivity, but in the presented method, the authors use SiCl4 to activate the carboxylic acid, permitting the use of only a catalytic amount of a chiral Lewis base to achieve high enantioselectivity.