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 Maijs 2017
Accepted
30 Jūl. 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
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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