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Issue 4, 2016
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Asymmetric addition of α-branched cyclic ketones to allenamides catalyzed by a chiral phosphoric acid

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Abstract

We describe the asymmetric addition of unactivated α-branched cyclic ketones to allenamides catalyzed by a chiral phosphoric acid, generating an all-carbon quaternary stereocenter with broad substrate scope and high enantioselectivity. The products are easily transformed into their corresponding 1,5- and 1,4-ketoaldehyde derivatives, which are both important building blocks in organic synthesis.

Graphical abstract: Asymmetric addition of α-branched cyclic ketones to allenamides catalyzed by a chiral phosphoric acid

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Article information


Submitted
04 Nov 2015
Accepted
12 Dec 2015
First published
19 Jan 2016

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

Chem. Sci., 2016,7, 2653-2656
Article type
Edge Article
Author version available

Asymmetric addition of α-branched cyclic ketones to allenamides catalyzed by a chiral phosphoric acid

X. Yang and F. D. Toste, Chem. Sci., 2016, 7, 2653
DOI: 10.1039/C5SC04202J

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