Stereoselective aza-Darzens reactions of tert-butanesulfinimines: convenient access to chiral aziridines

被引：25

作者：

Sola, Toni Moragas ^{[1
]}

Churcher, Ian ^{[2
]}

Lewis, William ^{[1
]}

Stockman, Robert A. ^{[1
]}

机构：

[1] Univ Nottingham, Sch Chem, Nottingham NG7 2RD, England

[2] GlaxoSmithKline Inc, Stevenage SG1 2NY, Herts, England

来源：

ORGANIC & BIOMOLECULAR CHEMISTRY | 2011年 / 9卷 / 14期

基金：

英国工程与自然科学研究理事会;

关键词：

N-SULFINYL IMINES; ASYMMETRIC-SYNTHESIS; ENANTIOPURE SULFOXIDES; SULFINIMINES; SULFINAMIDES; EPOXIDES; NITROGEN; AMINES;

D O I：

10.1039/c1ob05561e

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Stereoselective synthesis of 2,3-di- and 2,2',3-tri-substituted aziridines in good yields and excellent diastereoselectivities are achieved through aza-Darzens reactions of a range of tert-butanesulfinyl aldimines and ketimines with ethyl bromoacetate.

引用

页码：5034 / 5035

页数：2

共 31 条

[21] Synthesis and Applications of tert-Butanesulfinamide [J].

Robak, MaryAnn T. ;

Herbage, Melissa A. ;

Ellman, Jonathan A. .

CHEMICAL REVIEWS, 2010, 110 (06) :3600-3740

[22] Multicomponent Synthesis of Chiral Sulfinimines [J].

Roe, Caroline ;

Hobbs, Heather ;

Stockman, Robert A. .

CHEMISTRY-A EUROPEAN JOURNAL, 2011, 17 (09) :2704-2708

[23] Convenient synthesis of chiral non-racemic S-mesityl sulfinimines [J].

Sasraku-Neequaye, Leonid ;

MacPherson, David ;

Stockman, Robert A. .

TETRAHEDRON LETTERS, 2008, 49 (07) :1129-1132

[24] Catalytic, Enantioselective Ring Opening of Aziridines [J].

Schneider, Christoph .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (12) :2082-2084

[25]

Senanayake CH, 2005, ALDRICHIM ACTA, V38, P93

[26] Synthesis and reactivity of C-heteroatom-substituted aziridines [J].

Singh, Girija S. ;

D'hooghe, Matthias ;

De Kimpe, Norbert .

CHEMICAL REVIEWS, 2007, 107 (05) :2080-2135

[27] Aziridines: epoxides' ugly cousins? [J].

Sweeney, JB .

CHEMICAL SOCIETY REVIEWS, 2002, 31 (05) :247-258

[28]

SWEENEY JB, 2008, COMPOUNDS ONE SATURA, P643

[29] 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

[30] Advances in nitrogen transfer reactions involving aziridines [J].

Watson, IDG ;

Yu, LL ;

Yudin, AK .

ACCOUNTS OF CHEMICAL RESEARCH, 2006, 39 (03) :194-206

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