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

Choudhury, Abhijnan Ray and Manna, Madhu Sudan and Mukherjee, Santanu (2017) Nitro-enabled catalytic enantioselective formal umpolung alkenylation of beta-ketoesters. In: CHEMICAL SCIENCE, 8 (9). pp. 6686-6690.

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Official URL: http://doi.org/10.1039/c7sc02232h

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 beta-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.

Item Type: Journal Article
Additional Information: Copy right for this article belongs to the ROYAL SOC CHEMISTRY, THOMAS GRAHAM HOUSE, SCIENCE PARK, MILTON RD, CAMBRIDGE CB4 0WF, CAMBS, ENGLAND
Department/Centre: Division of Chemical Sciences > Organic Chemistry
Depositing User: Id for Latest eprints
Date Deposited: 16 Sep 2017 06:25
Last Modified: 16 Sep 2017 06:25
URI: http://eprints.iisc.ac.in/id/eprint/57793

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