Catalytic asymmetric [4 + 2] cycloadditions and Hosomi-Sakurai reactions of α-alkylidene β-keto imides

Kohei Orimoto, Harufumi Oyama, Yuki Namera, Takashi Niwa, Masahisa Nakada

Research output: Contribution to journalArticle

29 Citations (Scopus)

Abstract

Highly enantioselective catalytic asymmetric reactions of rationally designed α-alkylidene β-keto imides are described. The [4 + 2] cycloadditions and Hosomi-Sakurai reactions of α-alkylidene β-keto imides proceed with high enantioselectivity and yield. The [4 + 2] cycloadditions of the imides with various dienes afford products bearing an all-carbon quaternary stereogenic center at the ring junction. α-Alkylidene β-keto imides should be useful for the enantioselective total synthesis of natural products and other catalytic asymmetric applications.

Original languageEnglish
Pages (from-to)768-771
Number of pages4
JournalOrganic Letters
Volume15
Issue number4
DOIs
Publication statusPublished - 2013 Feb 15

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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