An Organocatalytic Kinetic Resolution of Aziridines by Thiol Nucleophiles

Song Sun; Zhaobin Wang; Shijia Li; Cong Zhou; Lijuan Song; Hai Huang; Jianwei Sun

doi:10.1021/acs.orglett.0c04074

An Organocatalytic Kinetic Resolution of Aziridines by Thiol Nucleophiles

Song Sun
, Zhaobin Wang
, Shijia Li
, Cong Zhou
, Lijuan Song
, Hai Huang^*
, Jianwei Sun^*

^*Corresponding author for this work

Research output: Contribution to journal › Article › peer-review

17 Scopus citations

Abstract

We report the first organocatalytic kinetic resolution of unactivated aziridines by sulfur nucleophiles with excellent enantioselectivity. A suitable chiral phosphoric acid was found to catalyze the intermolecular ring opening under mild conditions, furnishing a range of highly enantioenriched β-amino thioethers and aziridines, both of which are useful synthetic building blocks.

Original language	English
Pages (from-to)	554-558
Number of pages	5
Journal	Organic Letters
Volume	23
Issue number	2
DOIs	https://doi.org/10.1021/acs.orglett.0c04074
State	Published - 15 Jan 2021
Externally published	Yes

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10.1021/acs.orglett.0c04074

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title = "An Organocatalytic Kinetic Resolution of Aziridines by Thiol Nucleophiles",

abstract = "We report the first organocatalytic kinetic resolution of unactivated aziridines by sulfur nucleophiles with excellent enantioselectivity. A suitable chiral phosphoric acid was found to catalyze the intermolecular ring opening under mild conditions, furnishing a range of highly enantioenriched β-amino thioethers and aziridines, both of which are useful synthetic building blocks.",

author = "Song Sun and Zhaobin Wang and Shijia Li and Cong Zhou and Lijuan Song and Hai Huang and Jianwei Sun",

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T1 - An Organocatalytic Kinetic Resolution of Aziridines by Thiol Nucleophiles

AU - Sun, Song

AU - Wang, Zhaobin

AU - Li, Shijia

AU - Zhou, Cong

AU - Song, Lijuan

AU - Huang, Hai

AU - Sun, Jianwei

PY - 2021/1/15

Y1 - 2021/1/15

N2 - We report the first organocatalytic kinetic resolution of unactivated aziridines by sulfur nucleophiles with excellent enantioselectivity. A suitable chiral phosphoric acid was found to catalyze the intermolecular ring opening under mild conditions, furnishing a range of highly enantioenriched β-amino thioethers and aziridines, both of which are useful synthetic building blocks.

AB - We report the first organocatalytic kinetic resolution of unactivated aziridines by sulfur nucleophiles with excellent enantioselectivity. A suitable chiral phosphoric acid was found to catalyze the intermolecular ring opening under mild conditions, furnishing a range of highly enantioenriched β-amino thioethers and aziridines, both of which are useful synthetic building blocks.

UR - https://www.scopus.com/pages/publications/85100069047

U2 - 10.1021/acs.orglett.0c04074

DO - 10.1021/acs.orglett.0c04074

M3 - 文章

C2 - 33382271

AN - SCOPUS:85100069047

SN - 1523-7060

VL - 23

SP - 554

EP - 558

JO - Organic Letters

JF - Organic Letters

IS - 2

ER -

An Organocatalytic Kinetic Resolution of Aziridines by Thiol Nucleophiles

Abstract

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