Towards reaction selectivities of imines and aziridines

被引:59
作者
Hou, XL
Wu, J
Fan, RF
Ding, CH
Luo, ZB
Dai, LX
机构
[1] Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Organomet Chem, Shanghai 200032, Peoples R China
[2] Chinese Acad Sci, Shanghai Inst Organ Chem, Shanghai Hong Kong Joint Lab Chem Synth, Shanghai 200032, Peoples R China
关键词
transformations; imines; aziridines; mild conditions;
D O I
10.1055/s-2006-926220
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Several simple and convenient transformations of imines and aziridines under mild conditions have been developed, rendering access to several kinds of beta-amino derivatives, alpha-amino nitriles and phosphonates, aziridines, and conjugated dienes from imines and aziridines under neutral and metal-free conditions very conveniently. High stereoselectivities are realized in most reactions based upon mechanistic considerations.
引用
收藏
页码:181 / 193
页数:13
相关论文
共 76 条
[1]   Catalytic, asymmetric sulfur ylide-mediated epoxidation of carbonyl compounds: Scope, selectivity, and applications in synthesis [J].
Aggarwal, VK ;
Winn, CL .
ACCOUNTS OF CHEMICAL RESEARCH, 2004, 37 (08) :611-620
[2]  
Aggarwal VK, 1998, SYNLETT, P329
[3]   Unraveling the mechanism of epoxide formation from sulfur ylides and aldehydes [J].
Aggarwal, VK ;
Harvey, JN ;
Richardson, J .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (20) :5747-5756
[4]   Additions of stabilised and semi-stabilised sulfur ylides to tosyl protected imines: Are they under kinetic or thermodynamic control? [J].
Aggarwal, VK ;
Charmant, JPH ;
Ciampi, C ;
Hornby, JM ;
O'Brien, CJ ;
Hynd, G ;
Parsons, R .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2001, (23) :3159-3166
[5]  
Aggarwal VK, 2001, ANGEW CHEM INT EDIT, V40, P1430, DOI 10.1002/1521-3773(20010417)40:8<1430::AID-ANIE1430>3.0.CO
[6]  
2-W
[7]   Metal-catalyzed addition of phosphine and methanesulfonic acid to alkyne [J].
Arisawa, M ;
Yamaguchi, M .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (10) :2387-2388
[8]   Mechanically induced solid-state generation of phosphorus ylides and the solvent-free Wittig reaction [J].
Balema, VP ;
Wiench, JW ;
Pruski, M ;
Pecharsky, VK .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (22) :6244-6245
[9]   Additions of organometallic reagents to C=N bonds: Reactivity and selectivity [J].
Bloch, R .
CHEMICAL REVIEWS, 1998, 98 (04) :1407-1438
[10]   ASYMMETRIC STRECKER SYNTHESIS USING ENANTIOPURE SULFINIMINES - A CONVENIENT SYNTHESIS OF ALPHA-AMINO-ACIDS [J].
DAVIS, FA ;
REDDY, RE ;
PORTONOVO, PS .
TETRAHEDRON LETTERS, 1994, 35 (50) :9351-9354