Synthesis of N,O-heterocycles by intramolecular conjugate addition of a hydroxylamine

被引:17
作者
Bates, Roderick W. [1 ]
Snell, Robert H. [1 ]
Winbush, SusAnn [2 ]
机构
[1] Nanyang Technol Univ, Div Chem & Biol Chem, Sch Phys & Math Sci, Singapore 637371, Singapore
[2] Chulabhorn Res Inst, Med Chem Lab, Bangkok 10210, Thailand
关键词
Michael addition; hydroxylamine; oxazine;
D O I
10.1055/s-2008-1072650
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Isoxazolidines and tetrahydro-1,2-oxazines were produced by a tandem deprotection-intramolecular Michael addition of hydroxylamines. For tetrahydrooxazine formation, high stereoselectivity was observed, even when a quaternary centre was formed.
引用
收藏
页码:1042 / 1044
页数:3
相关论文
共 13 条
[1]   Michael addition of N- and O-centred nucleophiles to tethered acrylates. The role of double bond geometry in controlling the diastereoselectivity of cyclisations leading to 2,6-disubstituted tetrahydropyrans and piperidines [J].
Banwell, MG ;
Bui, CT ;
Pham, HTT ;
Simpson, GW .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1996, (10) :967-969
[2]   Synthesis of diospongin A [J].
Bates, Roderick W. ;
Song, Ping .
TETRAHEDRON, 2007, 63 (21) :4497-4499
[3]   Syntheses of the sedum and related alkaloids [J].
Bates, RW ;
Sa-Ei, K .
TETRAHEDRON, 2002, 58 (30) :5957-5978
[4]   O-alkenyl hydroxylamines:: A new concept for cyclofunctionalization [J].
Bates, RW ;
Sa-Ei, K .
ORGANIC LETTERS, 2002, 4 (24) :4225-4227
[5]   A short and efficient synthesis of (-)-diospongin A [J].
Bressy, Cyril ;
Allais, Florent ;
Cossy, Janine .
SYNLETT, 2006, (20) :3455-3456
[6]   A general model for selectivity in olefin cross metathesis [J].
Chatterjee, AK ;
Choi, TL ;
Sanders, DP ;
Grubbs, RH .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (37) :11360-11370
[7]   Recent developments in olefin cross-metathesis [J].
Connon, SJ ;
Blechert, S .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2003, 42 (17) :1900-1923
[8]  
GROCHOWSKI E, 1976, SYNTHESIS-STUTTGART, P682
[9]  
Janza B, 2002, SYNTHESIS-STUTTGART, P2117
[10]   Surprisingly efficient catalytic Cr-mediated coupling reactions [J].
Namba, K ;
Wang, JS ;
Cui, S ;
Kishi, Y .
ORGANIC LETTERS, 2005, 7 (24) :5421-5424