Convenient synthesis of chiral non-racemic S-mesityl sulfinimines

被引：9

作者：

Sasraku-Neequaye, Leonid ^{[1
]}

MacPherson, David ^{[2
]}

Stockman, Robert A. ^{[1
]}

机构：

[1] Univ E Anglia, Sch Chem Sci & Pharm, Norwich NR4 7TJ, Norfolk, England

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

来源：

TETRAHEDRON LETTERS | 2008年 / 49卷 / 07期

基金：

英国工程与自然科学研究理事会;

关键词：

D O I：

10.1016/j.tetlet.2007.12.067

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A direct multi-component coupling of (2S,4R,5S)-N-tosyl-4-methyl-5-phenyl-1,2,3-oxathiozolidine-2-oxide with mesityl magnesium bromide, LHMDS and a range of aldehydes produces chiral sulfinimines in essentially optically pure form in an operationally simple single pot procedure. (C) 2008 Elsevier Ltd. All rights reserved.

引用

页码：1129 / 1132

页数：4

共 15 条

[1] ASYMMETRIC INDUCTION IN THE REDUCTION OF OPTICALLY-ACTIVE N-ALKYLIDENESULFINAMIDES BY METAL-HYDRIDES - A NEW, EFFICIENT ENANTIOSELECTIVE ROUTE TO CHIRAL AMINES [J].

ANNUNZIATA, R ;

CINQUINI, M ;

COZZI, F .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1982, (02) :339-343

[2] Catalytic asymmetric oxidation of tert-butyl disulfide.: Synthesis of tert-butanesulfinamides, tert-butyl sulfoxides, and tert-butanesulfinimines [J].

Cogan, DA ;

Liu, GC ;

Kim, KJ ;

Backes, BJ ;

Ellman, JA .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (32) :8011-8019

[3] Improved asymmetric synthesis of aziridine 2-phosphonates using (S)-(+)-2,4,6-trimethylphenylsulfinamide [J].

Davis, FA ;

Ramachandar, T ;

Wu, YZ .

JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (18) :6894-6898

[4] Asymmetric synthesis and properties of sulfinimines (thiooxime S-oxides) [J].

Davis, FA ;

Reddy, RE ;

Szewczyk, JM ;

Reddy, GV ;

Portonovo, PS ;

Zhang, HM ;

Fanelli, D ;

Reddy, RT ;

Zhou, P ;

Carroll, PJ .

JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (08) :2555-2563

[5] Improved synthesis of enantiopure sulfinimines (thiooxime S-oxides) from p-toluenesulfinamide and aldehydes and ketones [J].

Davis, FA ;

Zhang, YL ;

Andemichael, Y ;

Fang, TA ;

Fanelli, DL ;

Zhang, HM .

JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (04) :1403-1406

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

Davis, Franklin A. .

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

[7]

HAN Z, 2003, ANGEW CHEM, V115, P2078

[8] 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

[9] 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

[10] First application of tunable alkyl or aryl sulfinamides to the stereoselective synthesis of a chiral amine:: Asymmetric synthesis of (R)-didesmethylsibutramine ((R)-DDMS) using (R)-triethylmethylsulfinamide ((R)-TESA) [J].

Han, ZX ;

Krishnamurthy, D ;

Pflum, D ;

Grover, P ;

Wald, SA ;

Senanayake, CH .

ORGANIC LETTERS, 2002, 4 (23) :4025-4028

← 1 2 →