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

doi:10.1016/S0040-4039(02)00361-1

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 Center for Advanced Particle Physics

Research output: Contribution to journal › Article

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 language	English
Pages (from-to)	2735-2739
Number of pages	5
Journal	Tetrahedron Letters
Volume	43
Issue number	15
DOIs	https://doi.org/10.1016/S0040-4039(02)00361-1
Publication status	Published - Apr 8 2002

Fingerprint

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

Sugihara, H., Daikai, K., Jin, X. L., Furuno, H., & Inanaga, J. (2002). Catalytic conversion of conjugated enones into optically active α-keto aziridines using chiral rare earth metal complexes. Tetrahedron Letters, 43(15), 2735-2739. https://doi.org/10.1016/S0040-4039(02)00361-1

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 journal › Article

Sugihara, H, Daikai, K, Jin, XL, Furuno, H & Inanaga, J 2002, 'Catalytic conversion of conjugated enones into optically active α-keto aziridines using chiral rare earth metal complexes', Tetrahedron Letters, vol. 43, no. 15, pp. 2735-2739. https://doi.org/10.1016/S0040-4039(02)00361-1

Sugihara H, Daikai K, Jin XL, Furuno H, Inanaga J. Catalytic conversion of conjugated enones into optically active α-keto aziridines using chiral rare earth metal complexes. Tetrahedron Letters. 2002 Apr 8;43(15):2735-2739. https://doi.org/10.1016/S0040-4039(02)00361-1

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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10.1016/S0040-4039(02)00361-1