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

Fingerprint

Anhydrides
Alcohols
Thiourea
Kinetics
Enantioselectivity
Catalysts
glutaric anhydride
cinchonidine

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Organocatalytic kinetic resolution of racemic secondary nitroallylic alcohols combined with simultaneous desymmetrization of prochiral cyclic anhydrides. / Roy, Suparna; Chen, Kan Fu; Gurubrahamam, Ramani; Chen, Kwunmin.

In: Journal of Organic Chemistry, Vol. 79, No. 19, 03.10.2014, p. 8955-8959.

Research output: Contribution to journalArticle

@article{783fe5c6b02645b2931864152fa72ba3,
title = "Organocatalytic kinetic resolution of racemic secondary nitroallylic alcohols combined with simultaneous desymmetrization of prochiral cyclic anhydrides",
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.",
author = "Suparna Roy and Chen, {Kan Fu} and Ramani Gurubrahamam and Kwunmin Chen",
year = "2014",
month = "10",
day = "3",
doi = "10.1021/jo501882q",
language = "English",
volume = "79",
pages = "8955--8959",
journal = "Journal of Organic Chemistry",
issn = "0022-3263",
publisher = "American Chemical Society",
number = "19",

}

TY - JOUR

T1 - Organocatalytic kinetic resolution of racemic secondary nitroallylic alcohols combined with simultaneous desymmetrization of prochiral cyclic anhydrides

AU - Roy, Suparna

AU - Chen, Kan Fu

AU - Gurubrahamam, Ramani

AU - Chen, Kwunmin

PY - 2014/10/3

Y1 - 2014/10/3

N2 - 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.

AB - 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.

UR - http://www.scopus.com/inward/record.url?scp=84907758495&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=84907758495&partnerID=8YFLogxK

U2 - 10.1021/jo501882q

DO - 10.1021/jo501882q

M3 - Article

AN - SCOPUS:84907758495

VL - 79

SP - 8955

EP - 8959

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

SN - 0022-3263

IS - 19

ER -