Catalytic conversion of conjugated enones into optically active α-keto aziridines using chiral rare earth metal complexes

Hiroyasu Sugihara, Kazuhiro Daikai, Xiu Lan Jin, Hiroshi Furuno, Junji Inanaga

Research output: Contribution to journalArticle

46 Citations (Scopus)

Abstract

Optically active N-unsubstituted α-keto aziridines 2 were synthesized from conjugated enones 1 via the Sc[(R)-BNP]3-catalyzed enantioselective Michael addition of O-methylhydroxylamine followed by the La(O-i-Pr)3-catalyzed ring closure of the corresponding β-methoxyamino ketones 3. A remarkably high asymmetric amplification was observed during the Michael addition, and notable kinetic resolution was also realized during the ring closure reaction when a La(O-i-Pr)3-(R)-BINOL catalyst system was employed.

Original languageEnglish
Pages (from-to)2735-2739
Number of pages5
JournalTetrahedron Letters
Volume43
Issue number15
DOIs
Publication statusPublished - Apr 8 2002

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Rare Earth Metals
Aziridines
Coordination Complexes
Ketones
Amplification
Catalysts
Kinetics
naphthol BINOL
methoxyamine

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

Cite this

Catalytic conversion of conjugated enones into optically active α-keto aziridines using chiral rare earth metal complexes. / Sugihara, Hiroyasu; Daikai, Kazuhiro; Jin, Xiu Lan; Furuno, Hiroshi; Inanaga, Junji.

In: Tetrahedron Letters, Vol. 43, No. 15, 08.04.2002, p. 2735-2739.

Research output: Contribution to journalArticle

Sugihara, Hiroyasu ; Daikai, Kazuhiro ; Jin, Xiu Lan ; Furuno, Hiroshi ; Inanaga, Junji. / Catalytic conversion of conjugated enones into optically active α-keto aziridines using chiral rare earth metal complexes. In: Tetrahedron Letters. 2002 ; Vol. 43, No. 15. pp. 2735-2739.
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