Asymmetric Trisubstituted Aziridination of Aldimines and Ketimines using N-α-Diazoacyl Camphorsultams

被引：23

作者：

Hashimoto, Takuya ^{[1
]}

Nakatsu, Hiroki ^{[1
]}

Yamamoto, Kumiko ^{[1
]}

Watanabe, Shogo ^{[1
]}

Maruoka, Keiji ^{[1
]}

机构：

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

来源：

CHEMISTRY-AN ASIAN JOURNAL | 2011年 / 6卷 / 02期

关键词：

asymmetric synthesis; aziridine; camphorsultam; chiral auxiliaries; diazo compounds; CARBON QUATERNARY CENTER; AMINO-ACIDS; STEREOSELECTIVE-SYNTHESIS; ENANTIOSELECTIVE SYNTHESIS; CATALYTIC AZIRIDINATION; MANNICH REACTIONS; LEWIS-ACID; CONSTRUCTION; IMINES; VAPOL;

D O I：

10.1002/asia.201000604

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The acid-catalyzed reaction of diazoacetates and aldimines (Brookhart-Templeton aziridination) is now recognized as a reliable method to provide enantiomerically enriched disubstituted aziridines, thus owing to the development of asymmetric catalysis. However, the extension of this method to prepare trisubstituted aziridines has not been explored to date, even for racemic products. In this context, and considering their synthetic importance and lack of alternative direct synthetic methods, we recently launched a program to realize this unmet challenge. Herein, we report a detailed study, which led to the establishment of a highly stereoselective synthesis for various trisubstituted aziridines, building on the use of N-alpha-diazoacyl camphorsultams as a key component.

引用

页码：607 / 613

页数：7

共 36 条

[21] Enantio- and diastereoselective construction of α,α-disubstituted α-amino acids for the synthesis of biologically active compounds [J].

Ohfune, Y ;

Shinada, T .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2005, 2005 (24) :5127-5143

[22]

Patwardhan A. P., 2005, ANGEW CHEM, V117, P6325

[23] Highly diastereoselective alkylation of aziridine-2-carboxylate esters: Enantioselective synthesis of LFA-1 antagonist BIRT-377 [J].

Patwardhan, AP ;

Pulgam, VR ;

Zhang, Y ;

Wulff, WD .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (38) :6169-6172

[24] Synthesis of asymmetric iron-pybox complexes and their application to aziridine forming reactions [J].

Redlich, M ;

Hossain, MM .

TETRAHEDRON LETTERS, 2004, 45 (49) :8987-8990

[25] Aziridine Synthesis via Nucleophilic Attack of Carbene Equivalents on Imines: the Aza-Darzens Reaction [J].

Sweeney, Joseph .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2009, 2009 (29) :4911-4919

[26] Direct enantio- and diastereoselective Mannich reactions of malonate and β-keto esters with N-Boc and N-Cbz aldimines catalysed by a bifunctional cinchonine derivative [J].

Tillman, AL ;

Ye, JX ;

Dixon, DJ .

CHEMICAL COMMUNICATIONS, 2006, (11) :1191-1193

[27] Novel synthesis of 4-carboxymethyl 5-alkyl/aryl oxazolidin-2-ones by rearrangement of 2-carboxymethyl 3-alkyl/aryl N-tert-butoxycarbonyl aziridines [J].

Tomasini, C ;

Vecchione, A .

ORGANIC LETTERS, 1999, 1 (13) :2153-2156

[28] Recent approaches towards the asymmetric synthesis of α,α-disubstituted α-amino acids [J].

Vogt, Henning ;

Braese, Stefan .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2007, 5 (03) :406-430

[29] Asymmetric catalytic Mannich reactions catalyzed by urea derivatives:: Enantioselective synthesis of β-aryl-β-amino acids [J].

Wenzel, AG ;

Jacobsen, EN .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (44) :12964-12965

[30] The bronsted acid-catalyzed direct aza-darzens synthesis of N-alkyl cis-aziridines [J].

Williams, AL ;

Johnston, JN .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (06) :1612-1613

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