Asymmetric induction via short-lived chiral enolates with a chiral C-O axis

Tomoyuki Yoshimura, Keisuke Tomohara, Takeo Kawabata

Research output: Contribution to journalArticle

17 Citations (Scopus)

Abstract

A novel method has been developed for the asymmetric cyclization of alkyl aryl ethers. The reactions were assumed to proceed via short-lived chiral enolate intermediates with a chiral C-O axis to give cyclic ethers with tetrasubstituted carbon in up to 99% ee. The half-life of racemization of the chiral enolate intermediate was roughly estimated to be ∼1 s at -78 C.

Original languageEnglish
Pages (from-to)7102-7105
Number of pages4
JournalJournal of the American Chemical Society
Volume135
Issue number19
DOIs
Publication statusPublished - May 15 2013
Externally publishedYes

All Science Journal Classification (ASJC) codes

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

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