Issue 4, 2016

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

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

Supplementary files

Article information

Article type
Edge Article
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
Creative Commons BY license

Chem. Sci., 2016,7, 2653-2656

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

This article is licensed under a Creative Commons Attribution 3.0 Unported Licence. You can use material from this article in other publications without requesting further permissions from the RSC, provided that the correct acknowledgement is given.

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