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

[1]

Aggarwal V.K., 2006, Aziridines and Epoxides in Organic Synthesis, P1

[2] Stereospecific Ring Expansion of Chiral Vinyl Aziridines [J].

Brichacek, Matthew ;

Villalobos, Mauricio Navarro ;

Plichta, Alexandra ;

Njardarson, Jon T. .

ORGANIC LETTERS, 2011, 13 (05) :1110-1113

[3] Aza-Darzens asymmetric synthesis of N-(p-toluenesulfinyl) aziridine 2-carboxylate esters from sulfinimines (N-sulfinyl imines) [J].

Davis, FA ;

Liu, H ;

Zhou, P ;

Fang, TN ;

Reddy, GV ;

Zhang, YL .

JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (20) :7559-7567

[4]

Davis FA, 1998, CHEM SOC REV, V27, P13

[5] Adventures in sulfur-nitrogen [J].

Davis, Franklin A. .

JOURNAL OF ORGANIC CHEMISTRY, 2006, 71 (24) :8993-9003

[6] N-tert-Butanesulfinyl imines:: Versatile intermediates for the asymmetric synthesis of amines [J].

Ellman, JA ;

Owens, TD ;

Tang, TP .

ACCOUNTS OF CHEMICAL RESEARCH, 2002, 35 (11) :984-995

[7] tert-Butanesulfinimines: structure, synthesis and synthetic applications [J].

Ferreira, Franck ;

Botuha, Candice ;

Chemla, Fabrice ;

Perez-Luna, Alejandro .

CHEMICAL SOCIETY REVIEWS, 2009, 38 (04) :1162-1186

[8]

HAN Z, 2003, ANGEW CHEM, V115, P2078

[9] Practical and highly stereoselective technology for preparation of enantiopure sulfoxides and sulfinamides utilizing activated and functionally differentiated N-sulfonyl-1,2,3-oxathiazolidine-2-oxide derivatives [J].

Han, ZX ;

Krishnamurthy, D ;

Grover, P ;

Fang, QK ;

Su, XP ;

Wilkinson, HS ;

Lu, ZH ;

Magiera, D ;

Senanayake, CH .

TETRAHEDRON, 2005, 61 (26) :6386-6408

[10] Effective tuning of the arene and alkanesulfinamides for highly enantioselective synthesis of (S)-4-chlorophenylphenylmethylamine, a key intermediate for antihistamic (S)-cetirizine [J].

Han, ZX ;

Krishnamurthy, D ;

Grover, P ;

Fang, QK ;

Pflum, DA ;

Senanayake, CH .

TETRAHEDRON LETTERS, 2003, 44 (22) :4195-4197

← 1 2 3 4 →