2-(trimethylsilyl)ethanesulfonyl (or SES) group in amine protection and activation

被引：47
作者：
Ribiere, Patrice
Declerck, Valerie
Martinez, Jean
Lamaty, Frederic
机构：
[1] Univ Montpellier I, CNRS, LAPP, F-34095 Montpellier 5, France
[2] Univ Montpellier 2, CNRS, LAPP, F-34095 Montpellier 5, France
来源：
CHEMICAL REVIEWS | 2006年 / 106卷 / 06期
关键词：
D O I：
10.1021/cr0300587
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
The 2-(trimethylsilyl)ethanesulfonyl (SES) group is an amine protecting group already described in several types of synthesis. Beyond the simple amine protection, the reagents derived from SES-NH2 give access to a large variety of amino compounds by direct introduction of SES-sulfonamide into a substrate. Stability, orthogonality, and mild conditions of deprotection, as well as activating properties, make the use of the SES protecting group in synthesis very attractive, competitive with the tosyl group.
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收藏
页码：2249 / 2269
页数：21
相关论文
共 143 条
[1]   Asymmetric sulfur ylide mediated aziridination: Application in the synthesis of the side chain of taxol [J].
Aggarwal, VK ;
Vasse, JL .
ORGANIC LETTERS, 2003, 5 (21) :3987-3990
[2]   Highly diastereoselective aziridination of imines with trimethylsilyldiazomethane.: Subsequent silyl substitution with electrophiles, ring opening, and metalation of C-silylaziridines -: A cornucopia of highly selective transformations [J].
Aggarwal, VK ;
Alonso, E ;
Ferrara, M ;
Spey, SE .
JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (07) :2335-2344
[3]   Scope and limitations in sulfur ylide mediated catalytic asymmetric aziridination of imines: use of phenyldiazomethane, diazoesters and diazoacetamides [J].
Aggarwal, VK ;
Ferrara, M ;
O'Brien, CJ ;
Thompson, A ;
Jones, RVH ;
Fieldhouse, R .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2001, (14) :1635-1643
[4]   A novel procedure for the synthesis of aziridines: application of Simmons-Smith reagents to aziridination [J].
Aggarwal, VK ;
Stenson, RA ;
Jones, RVH ;
Fieldhouse, R ;
Blacker, J .
TETRAHEDRON LETTERS, 2001, 42 (08) :1587-1589
[5]  
Aggarwal VK, 2001, ANGEW CHEM INT EDIT, V40, P1433, DOI 10.1002/1521-3773(20010417)40:8<1433::AID-ANIE1433>3.0.CO
[6]  
2-E
[7]   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
[8]   Highly selective aziridination of imines using trimethylsilyldiazomethane and applications of C-silylaziridines in synthesis [J].
Aggarwal, VK ;
Ferrara, M .
ORGANIC LETTERS, 2000, 2 (25) :4107-4110
[9]   Studies on total synthesis of the cytotoxic marine alkaloid agelastatin A [J].
Anderson, GT ;
Chase, CE ;
Koh, YH ;
Stien, D ;
Weinreb, SM ;
Shang, MY .
JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (22) :7594-7595
[10]  
Artman GD, 2001, SYNLETT, P232
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