N-alkylation and [2,3]-sigmatropic rearrangement of N-allyl alpha-amino esters

被引:20
作者
Coldham, I [1 ]
Middleton, ML [1 ]
Taylor, PL [1 ]
机构
[1] ICI PAINTS,SLOUGH SL2 5DS,BERKS,ENGLAND
来源
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1997年 / 20期
关键词
D O I
10.1039/a705550a
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
N-Alkylation of N-allyl alpha-amino esters and [2,3]-Stevens rearrangement occur in one pot on warming in the solvent DMF, with the bases K2CO3 and DBU; this in situ formation of the quaternary ammonium salts and rearrangement of the subsequent ylides gives N,N-dialkylated allyl glycine derivatives.
引用
收藏
页码:2951 / 2952
页数:2
相关论文
共 27 条
[1]   Synthesis and aza-[2,3]-Wittig rearrangements of vinylaziridines: Scope and limitations [J].
Ahman, J ;
Jarevang, T ;
Somfai, P .
JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (23) :8148-8159
[2]   The silicon-assisted aza-[2,3]-Wittig sigmatropic rearrangement [J].
Anderson, JC ;
Siddons, DC ;
Smith, SC ;
Swarbrick, ME .
JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (14) :4820-4823
[3]   AZA-[2,3]-WITTIG SIGMATROPIC REARRANGEMENT OF CROTYL AMINES [J].
ANDERSON, JC ;
SIDDONS, DC ;
SMITH, SC ;
SWARBRICK, ME .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1995, (18) :1835-1836
[4]  
[Anonymous], 1991, Comprehensive Organic Synthesis
[5]  
[Anonymous], 1991, COMPREHENSIVE ORGANI
[6]   [2,3] SIGMATROPIC REARRANGEMENT OF 1-VINYLIC TETRAHYDROISOQUINOLINE N-YLIDES AND N-OXIDES [J].
BAILEY, TS ;
BREMNER, JB ;
CARVER, JA .
TETRAHEDRON LETTERS, 1993, 34 (20) :3331-3334
[7]   INTRAMOLECULAR GENERATION AND REARRANGEMENT OF AMMONIUM YLIDES FROM COPPER CARBENOIDS - A GENERAL-METHOD FOR THE SYNTHESIS OF CYCLIC AMINES [J].
CLARK, JS ;
HODGSON, PB .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1994, (23) :2701-2702
[8]  
CLARK JS, 1995, TETRAHEDRON LETT, V36, P2519
[9]   AZA-WITTIG REARRANGEMENTS AND CYCLIZATIONS BY TRANSMETALATION OF N-BENZYLAMINOMETHYLSTANNANES [J].
COLDHAM, I .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1993, (12) :1275-1276
[10]   SYNTHESIS OF 4-PHENYLPIPERIDINES BY TANDEM WITTIG OLEFINATION-AZA-WITTIG REARRANGEMENT OF 2-BENZOYLAZIRIDINES [J].
COLDHAM, I ;
COLLIS, AJ ;
MOULD, RJ ;
RATHMELL, RE .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1995, (21) :2739-2745