Issue 4, 2015

Phase-transfer-catalyzed asymmetric desymmetrizations of cyclopentanones

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

Supplementary files

Article information

Article type
Research Article
Submitted
20 ⴷⵓⵊ 2014
Accepted
30 ⵉⵏⵏ 2015
First published
03 ⴱⵕⴰ 2015

Org. Chem. Front., 2015,2, 336-339

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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