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Issue 4, 2015
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Phase-transfer-catalyzed asymmetric desymmetrizations of cyclopentanones

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Abstract

Although various highly enantioselective transformations have been achieved under phase-transfer conditions, asymmetric desymmetrization of cyclic ketones is still a challenging reaction in the phase-transfer chemistry. In this context, we have developed asymmetric desymmetrization of meso-epoxy ketones under phase-transfer conditions. The epoxide-opening reaction was efficiently promoted by chiral bifunctional phase-transfer catalysts to give the corresponding cyclic ketones with high enantioselectivities. Furthermore, this reaction system was applied to asymmetric isomerization of cyclic ketone.

Graphical abstract: Phase-transfer-catalyzed asymmetric desymmetrizations of cyclopentanones

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Article information


Submitted
20 Dec 2014
Accepted
30 Jan 2015
First published
03 Feb 2015

Org. Chem. Front., 2015,2, 336-339
Article type
Research Article
Author version available

Phase-transfer-catalyzed asymmetric desymmetrizations of cyclopentanones

S. Shirakawa, T. Tokuda, S. B. J. Kan and K. Maruoka, Org. Chem. Front., 2015, 2, 336
DOI: 10.1039/C4QO00339J

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