Trans-Selective Asymmetric Aziridination of Diazoacetamides and N-Boc Imines Catalyzed by Axially Chiral Dicarboxylic Acid

被引：109

作者：

Hashimoto, Takuya ^{[1
]}

Uchiyama, Nanase ^{[1
]}

Maruoka, Keiji ^{[1
]}

机构：

[1] Kyoto Univ, Dept Chem, Grad Sch Sci, Sakyo Ku, Kyoto 6068502, Japan

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2008年 / 130卷 / 44期

关键词：

D O I：

10.1021/ja805635c

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Axially chiral dicarboxylic acid (R)-1d catalyzed reaction of diazoacetamides and N-Boc imines provided a novel organocatalytic means for the formation of enantiomerically enriched N-Boc protected trans aziridines.

引用

页码：14380 / +

页数：3

共 35 条

[1]

Aggarwal VK, 2001, ANGEW CHEM INT EDIT, V40, P1433, DOI 10.1002/1521-3773(20010417)40:8<1433::AID-ANIE1433>3.0.CO

[2]

2-E

[3] Novel catalytic and asymmetric process for aziridination mediated by sulfur ylides [J].

Aggarwal, VK ;

Thompson, A ;

Jones, RVH ;

Standen, MCH .

JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (24) :8368-8369

[4] Stereoselective synthesis of CF3-substituted aziridines by Lewis acid-mediated aziridination of aldimines with diazoacetates [J].

Akiyama, T ;

Ogi, S ;

Fuchibe, K .

TETRAHEDRON LETTERS, 2003, 44 (21) :4011-4013

[5] 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

[6]

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

[7] Lewis acid-catalyzed synthesis of aziridines [J].

Casarrubios, L ;

Perez, JA ;

Brookhart, M ;

Templeton, JL .

JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (24) :8358-8359

[8] Synthesis and reactivity of tungsten(II) methylene complexes [J].

Gunnoe, TB ;

Surgan, M ;

White, PS ;

Templeton, JL ;

Casarrubios, L .

ORGANOMETALLICS, 1997, 16 (22) :4865-4874

[9] Electrophilic tungsten(II) methylene carbene complexes: Adduct formation, methylene transfer, and catalysis of aziridine formation from imines and ethyl diazoacetate [J].

Gunnoe, TB ;

White, PS ;

Templeton, JL ;

Casarrubios, L .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (13) :3171-3172

[10] A new synthesis of aziridine-2-carboxylates:: Reaction of hexahydro-1,3,5-triazines or N-methoxymethylanilines with alkyl diazoacetates in the presence of Lewis acid [J].

Ha, HJ ;

Suh, JM ;

Kang, KH ;

Ahn, YG ;

Han, O .

TETRAHEDRON, 1998, 54 (5-6) :851-858

← 1 2 3 4 →