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

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48 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

All Science Journal Classification (ASJC) codes

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/S0040-4039(02)00361-1

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

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.",

author = "Hiroyasu Sugihara and Kazuhiro Daikai and Jin, {Xiu Lan} and Hiroshi Furuno and Junji Inanaga",

note = "Funding Information: This work was supported by a Grant-in-Aid for Scientific Research on Priority Areas from the Ministry of Education, Culture, Sports, Science and Technology, Japan and also by the Japan Society for the Promotion of Science.",

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doi = "10.1016/S0040-4039(02)00361-1",

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T1 - Catalytic conversion of conjugated enones into optically active α-keto aziridines using chiral rare earth metal complexes

AU - Sugihara, Hiroyasu

AU - Daikai, Kazuhiro

AU - Jin, Xiu Lan

AU - Furuno, Hiroshi

AU - Inanaga, Junji

N1 - Funding Information: This work was supported by a Grant-in-Aid for Scientific Research on Priority Areas from the Ministry of Education, Culture, Sports, Science and Technology, Japan and also by the Japan Society for the Promotion of Science.

PY - 2002/4/8

Y1 - 2002/4/8

N2 - 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.

AB - 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.

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M3 - Article

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JO - Tetrahedron Letters

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SN - 0040-4039

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ER -

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

Abstract

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