Carbene-catalyzed desymmetrization of 1,3-diols: Access to optically enriched tertiary alkyl chlorides

Bao Sheng Li; Yuhuang Wang; Rupert S.J. Proctor; Zhichao Jin; Yonggui Robin Chi

doi:10.1039/c6cc03345h

Carbene-catalyzed desymmetrization of 1,3-diols: Access to optically enriched tertiary alkyl chlorides

Bao Sheng Li, Yuhuang Wang, Rupert S.J. Proctor, Zhichao Jin, Yonggui Robin Chi^*

^*Corresponding author for this work

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

38 Citations (Scopus)

Abstract

The introduction of a chlorine atom to a carbon center in an enantioselective manner via conventional C-Cl bond formation is difficult. Here we report a new approach to this class of tertiary alkyl chlorides with high optical purities. Instead of forming a new C-Cl bond, our approach involves carbene-catalyzed desymmetrization of 2-chloro-1,3-diols as the key step to set up the chiral carbon center with excellent enantiomeric excess.

Original language	English
Pages (from-to)	8313-8316
Number of pages	4
Journal	Chemical Communications
Volume	52
Issue number	53
DOIs	https://doi.org/10.1039/c6cc03345h
Publication status	Published - 2016
Externally published	Yes

Bibliographical note

Publisher Copyright:
This journal is © 2016 The Royal Society of Chemistry.

ASJC Scopus Subject Areas

Electronic, Optical and Magnetic Materials
Catalysis
Ceramics and Composites
General Chemistry
Surfaces, Coatings and Films
Metals and Alloys
Materials Chemistry

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abstract = "The introduction of a chlorine atom to a carbon center in an enantioselective manner via conventional C-Cl bond formation is difficult. Here we report a new approach to this class of tertiary alkyl chlorides with high optical purities. Instead of forming a new C-Cl bond, our approach involves carbene-catalyzed desymmetrization of 2-chloro-1,3-diols as the key step to set up the chiral carbon center with excellent enantiomeric excess.",

author = "Li, {Bao Sheng} and Yuhuang Wang and Proctor, {Rupert S.J.} and Zhichao Jin and Chi, {Yonggui Robin}",

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doi = "10.1039/c6cc03345h",

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T1 - Carbene-catalyzed desymmetrization of 1,3-diols

T2 - Access to optically enriched tertiary alkyl chlorides

AU - Li, Bao Sheng

AU - Wang, Yuhuang

AU - Proctor, Rupert S.J.

AU - Jin, Zhichao

AU - Chi, Yonggui Robin

PY - 2016

Y1 - 2016

N2 - The introduction of a chlorine atom to a carbon center in an enantioselective manner via conventional C-Cl bond formation is difficult. Here we report a new approach to this class of tertiary alkyl chlorides with high optical purities. Instead of forming a new C-Cl bond, our approach involves carbene-catalyzed desymmetrization of 2-chloro-1,3-diols as the key step to set up the chiral carbon center with excellent enantiomeric excess.

AB - The introduction of a chlorine atom to a carbon center in an enantioselective manner via conventional C-Cl bond formation is difficult. Here we report a new approach to this class of tertiary alkyl chlorides with high optical purities. Instead of forming a new C-Cl bond, our approach involves carbene-catalyzed desymmetrization of 2-chloro-1,3-diols as the key step to set up the chiral carbon center with excellent enantiomeric excess.

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U2 - 10.1039/c6cc03345h

DO - 10.1039/c6cc03345h

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JO - Chemical Communications

JF - Chemical Communications

IS - 53

ER -

Carbene-catalyzed desymmetrization of 1,3-diols: Access to optically enriched tertiary alkyl chlorides

Abstract

Bibliographical note

ASJC Scopus Subject Areas

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