Phosphine-Catalyzed β,γ-Umpolung Domino Reaction of Allenic Esters: Facile Synthesis of Tetrahydrobenzofuranones Bearing a Chiral Tetrasubstituted Stereogenic Carbon Center

Shinobu Takizawa, Kenta Kishi, Yasushi Yoshida, Steffen Mader, Fernando Arteaga Arteaga, Shoukou Lee, Manabu Hoshino, Magnus Rueping, Makoto Fujita, Hiroaki Sasai*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

85 Scopus citations

Abstract

An enantio-, diastereo-, regio-, and chemoselective phosphine-catalyzed β,γ-umpolung domino reaction of allenic esters with dienones has been developed for the first time. The designed sequence, involving oxy-Michael and Rauhut-Currier reactions, produced highly functionalized tetrahydrobenzofuranones, bearing a chiral tetrasubstituted stereogenic center, in up to 96 % ee. Domino effect: An enantio-, diastereo-, regio-, and chemoselective phosphine-catalyzed β,γ-umpolung domino reaction of allenic esters with dienones has been developed for the first time. The designed sequence involving oxy-Michael and Rauhut-Currier reactions produced highly functionalized tetrahydrobenzofuranones bearing a chiral tetrasubstituted stereogenic center in up to 96 % ee.

Original languageEnglish (US)
Pages (from-to)15511-15515
Number of pages5
JournalAngewandte Chemie - International Edition
Volume54
Issue number51
DOIs
StatePublished - Dec 14 2015

Keywords

  • allenes
  • annulations
  • organocatalysis
  • phosphines
  • umpolung

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)

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