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Issue 4, 2014
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Asymmetric synthesis of chiral cycloalkenone derivatives via palladium catalysis

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Abstract

The palladium-catalyzed oxidative desymmetrization of meso-dibenzoates yields γ-benzoyloxy cycloalkenones in good yields and with excellent levels of enantioselectivity. These compounds serve as precursors to a broad range of substituted cycloalkenones, including well-established synthetic building blocks and elaborated cycloalkanone derivatives. The ability to prepare both enantiomers of the oxidative desymmetrization products enables a unified strategy toward stereochemically diverse epoxyquinoid natural products.

Graphical abstract: Asymmetric synthesis of chiral cycloalkenone derivatives via palladium catalysis

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Article information


Submitted
27 Nov 2013
Accepted
13 Jan 2014
First published
13 Jan 2014

This article is Open Access
All publication charges for this article have been paid for by the Royal Society of Chemistry

Chem. Sci., 2014,5, 1354-1360
Article type
Edge Article
Author version available

Asymmetric synthesis of chiral cycloalkenone derivatives via palladium catalysis

B. M. Trost, J. T. Masters, J. Lumb and D. Fateen, Chem. Sci., 2014, 5, 1354
DOI: 10.1039/C3SC53250J

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