Chiral rare earth metal complex-catalyzed conjugate addition of O-alkylhydroxylamines. An efficient synthetic entry into optically active 2-acyl aziridines

Xiu Lan Jin, Hiroyasu Sugihara, Kazuhiro Daikai, Hiroki Tateishi, Yong Zhi Jin, Hiroshi Furuno, Junji Inanaga

Research output: Contribution to journalArticle

68 Citations (Scopus)

Abstract

The conjugate addition of O-alkylhydroxylamines to α,β-unsaturated ketones is effectively catalyzed by chiral rare earth metal complexes to afford the corresponding β-amino ketones with high enantioselectivities (up to 99% ee) in almost quantitative yields, which are, upon treatment with a base catalyst, quantitatively converted into the 2-acyl aziridines without losing their enantiopurities. The protocol is highly practical thus providing an easy access to enantiopure 2-acyl aziridines and their derivatives in good quantities.

Original languageEnglish
Pages (from-to)8321-8329
Number of pages9
JournalTetrahedron
Volume58
Issue number41
DOIs
Publication statusPublished - Oct 7 2002

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Rare Earth Metals
Aziridines
Coordination Complexes
Ketones
Enantioselectivity
Derivatives
Catalysts

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

Cite this

Chiral rare earth metal complex-catalyzed conjugate addition of O-alkylhydroxylamines. An efficient synthetic entry into optically active 2-acyl aziridines. / Jin, Xiu Lan; Sugihara, Hiroyasu; Daikai, Kazuhiro; Tateishi, Hiroki; Jin, Yong Zhi; Furuno, Hiroshi; Inanaga, Junji.

In: Tetrahedron, Vol. 58, No. 41, 07.10.2002, p. 8321-8329.

Research output: Contribution to journalArticle

Jin, Xiu Lan ; Sugihara, Hiroyasu ; Daikai, Kazuhiro ; Tateishi, Hiroki ; Jin, Yong Zhi ; Furuno, Hiroshi ; Inanaga, Junji. / Chiral rare earth metal complex-catalyzed conjugate addition of O-alkylhydroxylamines. An efficient synthetic entry into optically active 2-acyl aziridines. In: Tetrahedron. 2002 ; Vol. 58, No. 41. pp. 8321-8329.
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