Catalytic enantioselective amination of silyl enol ethers using chiral dirhodium(II) carboxylates: Asymmetric formal synthesis of (-)-metazocine

Masahiro Anada, Masahiko Tanaka, Takuya Washio, Minoru Yamawaki, Takumi Abe, Shunichi Hashimoto

Research output: Contribution to journalArticlepeer-review

92 Citations (Scopus)

Abstract

(Chemical Equation Presented) Dirhodium(II) tetrakis[N- tetrafluorophthaloyl-(S)-tert-leucinate], Rh2(S-TFPTTL)4, is an exceptionally efficient catalyst for enantioselective aminations of silyl enol ethers derived from acyclic ketones or α,β-enones with [N-(2-nitrophenylsulfonyl)imino]phenyliodinane (NsN=IPh), providing N-(2-nitrophenylsulfonyl)-α-amino ketones in high yields and with enantioselectivities of up to 95% ee. The effectiveness of the present catalytic protocol has been demonstrated by an asymmetric formal synthesis of (-)-metazocine.

Original languageEnglish
Pages (from-to)4559-4562
Number of pages4
JournalOrganic Letters
Volume9
Issue number22
DOIs
Publication statusPublished - Oct 25 2007
Externally publishedYes

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

Fingerprint

Dive into the research topics of 'Catalytic enantioselective amination of silyl enol ethers using chiral dirhodium(II) carboxylates: Asymmetric formal synthesis of (-)-metazocine'. Together they form a unique fingerprint.

Cite this