Issue 9, 2017

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

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

Supplementary files

Article information

Article type
Edge Article
Submitted
17 5 2017
Accepted
30 7 2017
First published
02 8 2017
This article is Open Access

All publication charges for this article have been paid for by the Royal Society of Chemistry
Creative Commons BY-NC license

Chem. Sci., 2017,8, 6686-6690

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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