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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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Publication details

The article was received on 17 May 2017, accepted on 30 Jul 2017 and first published on 02 Aug 2017


Article type: Edge Article
DOI: 10.1039/C7SC02232H
Citation: Chem. Sci., 2017, Advance Article
  • Open access: Creative Commons BY-NC license
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    Nitro-enabled catalytic enantioselective formal umpolung alkenylation of β-ketoesters

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

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