Aziridinyl vinyl ketones from the asymmetric catalytic aziridination reaction

被引：32

作者：

Deng, Yonghong ^{[1
]}

Lee, Young Rok ^{[1
]}

Newman, Cory A. ^{[1
]}

Wulff, William D. ^{[1
]}

机构：

[1] Michigan State Univ, Dept Chem, E Lansing, MI 48824 USA

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2007年 / 2007卷 / 13期

关键词：

aziridines; asymmetric catalysis; Lewis acids;

D O I：

10.1002/ejoc.200601126

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Under the aegis of boron Lewis acids, prepared from either the vanol or vapol ligand, vinyl aziridinyl ketones can be obtained with a high degree of asymmetric induction from the catalytic asymmetric aziridination reaction (AZ) of imines and vinyl diazomethyl ketones. The products have potential as synthons for five-carbon chiral amines. ((C) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007).

引用

页码：2068 / 2071

页数：4

共 16 条

[1]

ALBAR HA, 1999, J ABDULAZIZ U, V11, P65

[2] Catalytic asymmetric aziridination with a chiral VAPOL-boron Lewis acid [J].

Antilla, JC ;

Wulff, WD .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (21) :5099-5100

[3]

Antilla JC, 2000, ANGEW CHEM INT EDIT, V39, P4518

[4] VAULTED BIARYLS AS CHIRAL LIGANDS FOR ASYMMETRIC CATALYTIC DIELS-ALDER REACTIONS [J].

BAO, JM ;

WULFF, WD ;

RHEINGOLD, AL .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (09) :3814-3815

[5] A COMPARISON OF DIELS-ALDER CATALYSTS GENERATED FROM LINEAR AND VAULTED BIARYLS AND BROMOBORANE-DIMETHYLSULFIDE COMPLEX [J].

BAO, JM ;

WULFF, WD .

TETRAHEDRON LETTERS, 1995, 36 (19) :3321-3324

[6] Synthesis and characterization of chiral diphosphine platinum(II) VANOL and VAPOL complexes [J].

Becker, JJ ;

White, PS ;

Gagné, MR .

ORGANOMETALLICS, 2003, 22 (16) :3245-3249

[7] Vaulted biaryls: Efficient ligands for the aluminum-catalyzed asymmetric Baeyer-Villiger reaction [J].

Bolm, C ;

Frison, JC ;

Zhang, Y ;

Wulff, WD .

SYNLETT, 2004, (09) :1619-1621

[8]

Danheiser RL, 1996, ORG SYNTH, V73, P134

[9] An examination of VANOL, VAPOL, and VAPOL derivatives as ligands for asymmetric catalytic Diels-Aider reactions [J].

Heller, Douglas P. ;

Goldberg, Daniel R. ;

Wu, Hongqiao ;

Wulff, William D. .

CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 2006, 84 (10) :1487-1503

[10] Positive cooperativity of product mimics in the asymmetric autoinduction of Diels-Alder reactions catalyzed by a VAPOL-aluminum catalyst [J].

Heller, DP ;

Goldberg, DR ;

Wulff, WD .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (43) :10551-10552

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