Synfacts 2009(10): 1125-1125  
DOI: 10.1055/s-0029-1217852
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart ˙ New York

Asymmetric Nucleophilic Epoxidation of Acyclic Trisubstituted Olefins

Contributor(s): Mark Lautens, Jacki Kitching
B.-F. Sun, R. Hong, Y.-B. Kang, L. Deng*
Brandeis University, Waltham, USA
Further Information

Publication History

Publication Date:
22 September 2009 (online)

Significance

The asymmetric epoxidation of acyclic trisubstituted olefins via a modified ­Seebach protocol (M. Aoki, D. Seebach Helv. Chim. Acta, 2001, 84, 187) is reported. This reaction was successfully applied to the first asymmetric total synthesis of (-)-plicatic acid (12 steps, 14% overall yield from eugenol).