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Issue 9, 2017
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Nitro-enabled catalytic enantioselective formal umpolung alkenylation of β-ketoesters

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Abstract

A formal umpolung strategy is presented for the enantioselective installation of an alkenyl group with a terminal double bond at a tertiary center. This one-pot two-step sequence relies on the unique features of the nitro group, which after inverting the polarity of the alkenylating agent toward the desired bond formation, itself serves as a leaving group. The application of this protocol to cyclic β-ketoesters results in densely functionalized products, bearing an all-carbon quaternary stereocenter including an alkenyl substituent with a terminal double bond, in high yields with excellent enantioselectivities.

Graphical abstract: Nitro-enabled catalytic enantioselective formal umpolung alkenylation of β-ketoesters

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Supplementary files

Article information


Submitted
17 May 2017
Accepted
30 Jul 2017
First published
02 Aug 2017

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

Chem. Sci., 2017,8, 6686-6690
Article type
Edge Article

Nitro-enabled catalytic enantioselective formal umpolung alkenylation of β-ketoesters

A. R. Choudhury, M. S. Manna and S. Mukherjee, Chem. Sci., 2017, 8, 6686
DOI: 10.1039/C7SC02232H

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