Nitro-enabled catalytic enantioselective formal: Umpolung alkenylation of β-ketoesters

Abhijnan Ray Choudhury, Madhu Sudan Manna, Santanu Mukherjee

Research output: Contribution to journalArticlepeer-review

6 Scopus citations

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.

Original languageEnglish (US)
Pages (from-to)6686-6690
Number of pages5
JournalChemical Science
Volume8
Issue number9
DOIs
StatePublished - 2017
Externally publishedYes

ASJC Scopus subject areas

  • Chemistry(all)

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