Organocatalytic kinetic resolution of racemic secondary nitroallylic alcohols combined with simultaneous desymmetrization of prochiral cyclic anhydrides

Suparna Roy; Kan-Fu Chen; Ramani Gurubrahamam; Kwunmin Chen

doi:10.1021/jo501882q

Organocatalytic kinetic resolution of racemic secondary nitroallylic alcohols combined with simultaneous desymmetrization of prochiral cyclic anhydrides

J Org Chem. 2014 Oct 3;79(19):8955-9. doi: 10.1021/jo501882q. Epub 2014 Sep 11.

Authors

Suparna Roy¹, Kan-Fu Chen, Ramani Gurubrahamam, Kwunmin Chen

Affiliation

¹ Department of Chemistry, National Taiwan Normal University , Taipei 11677, Taiwan.

PMID: 25211598
DOI: 10.1021/jo501882q

Abstract

This study describes an organocatalytic kinetic resolution of racemic secondary nitroallylic alcohols (2) combined with simultaneous desymmetrization of prochiral cyclic anhydrides (1). The experimental results revealed that enantioselective alcoholysis of 3-substituted glutaric anhydrides afforded hemiesters (3) with high levels of enantioselectivities (up to 99% ee) in the presence of cinchonidine-derived thiourea catalyst (IV). The highly optical enrichment (up to 95% ee) of (S)-nitroallylic alcohols (2) was recovered.