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Issue 53, 2016
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Carbene-catalyzed desymmetrization of 1,3-diols: access to optically enriched tertiary alkyl chlorides

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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.

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

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Article information


Submitted
21 Apr 2016
Accepted
08 Jun 2016
First published
08 Jun 2016

Chem. Commun., 2016,52, 8313-8316
Article type
Communication

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

B. Li, Y. Wang, R. S. J. Proctor, Z. Jin and Y. R. Chi, Chem. Commun., 2016, 52, 8313
DOI: 10.1039/C6CC03345H

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