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

Suparna Roy
, Kan Fu Chen
, Ramani Gurubrahamam
, Kwunmin Chen^*

^*此作品的通信作者

化學系

研究成果: 雜誌貢獻 › 期刊論文 › 同行評審

21 引文斯高帕斯（Scopus）

摘要

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.

原文	英語
頁（從 - 到）	8955-8959
頁數	5
期刊	Journal of Organic Chemistry
卷	79
發行號	19
DOIs	https://doi.org/10.1021/jo501882q
出版狀態	已發佈 - 2014 10月 3

ASJC Scopus subject areas

有機化學

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10.1021/jo501882q

其它文件與鏈接

CCDC 1018847: Experimental Crystal Structure Determination
Gurubrahamam, R. (Creator), Chen, K. (Creator) & Cheng, Y.-S. (Creator), Unknown Publisher, 2015
DOI: 10.5517/cc13661k, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/cc13661k&sid=DataCite
資料集: Dataset

引用此

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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",

note = "Publisher Copyright: {\textcopyright} 2014 American Chemical Society.",

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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.

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UR - https://www.scopus.com/pages/publications/84907758495#tab=citedBy

U2 - 10.1021/jo501882q

DO - 10.1021/jo501882q

M3 - Article

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SN - 0022-3263

VL - 79

SP - 8955

EP - 8959

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

IS - 19

ER -

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

摘要

ASJC Scopus subject areas

存取文件

其它文件與鏈接

指紋

資料集

CCDC 1018847: Experimental Crystal Structure Determination

引用此