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

Research output: Contribution to journalArticle

16 Citations (Scopus)

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.

Original languageEnglish
Pages (from-to)8955-8959
Number of pages5
JournalJournal of Organic Chemistry
Volume79
Issue number19
DOIs
Publication statusPublished - 2014 Oct 3

ASJC Scopus subject areas

  • Organic Chemistry

Fingerprint Dive into the research topics of 'Organocatalytic kinetic resolution of racemic secondary nitroallylic alcohols combined with simultaneous desymmetrization of prochiral cyclic anhydrides'. Together they form a unique fingerprint.

  • Cite this