A facile route to polysubstituted N-benzyl pyroglutamates

被引：52

作者：

Sun, PP ^{[1
]}

Chang, MY ^{[1
]}

Chiang, MY ^{[1
]}

Chang, NC ^{[1
]}

机构：

[1] Natl Sun Yat Sen Univ, Dept Chem, Kaohsiung 804, Taiwan

来源：

ORGANIC LETTERS | 2003年 / 5卷 / 10期

关键词：

D O I：

10.1021/ol0344164

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHICS] Base-induced coupling/cyclization reactions of a-sulfonylacetamide with various ethyl (2)-2-bromo-2-propenoates have been carried out. The polysubstituted pyroglutamate carbon skeleton, with three contiguous asymmetric centers, was built up in one step. A ring-closure mechanism is proposed for the reactions.

引用

页码：1761 / 1763

页数：3

共 33 条

[1] CARBON-CARBON BOND FORMATION VIA N-TOSYLIMINIUM IONS [J].

AHMAN, J ;

SOMFAI, P .

TETRAHEDRON, 1992, 48 (43) :9537-9544

[2] Synthesis of a potent (±)-4-(2-hydroxyphenyl) analogue of the acromelic acids by dearomatising cyclisation of a lithiated N-p-methoxybenzyl-4-methoxy-l-naphthamide [J].

Ahmed, A ;

Bragg, RA ;

Clayden, J ;

Tchabanenko, K .

TETRAHEDRON LETTERS, 2001, 42 (20) :3407-3410

[3] A NEW SYNTHETIC EQUIVALENT OF THE GLUTAMIC-ACID GAMMA-ANION AND ITS APPLICATION TO THE SYNTHESIS OF S-(+)-GAMMA-CARBOXYGLUTAMIC ACID [J].

ATTWOOD, MR ;

CARR, MG ;

JORDAN, S .

TETRAHEDRON LETTERS, 1990, 31 (02) :283-284

[4] Regioselective reduction of N-alkyl-3-sulfonyl glutarimides.: Synthesis of 3,4-dihydro-3-tosylpyridin-2-ones [J].

Chang, BR ;

Chen, CY ;

Chang, NC .

TETRAHEDRON LETTERS, 2002, 43 (17) :3233-3235

[5]

Chang MY, 2002, HETEROCYCLES, V57, P2321

[6]

Chang MY, 2003, HETEROCYCLES, V60, P99

[7] Synthetic study of 4-substituted piperidine ring in elarofiban, RWJ-50042, tirofiban and paroxetine [J].

Chang, MY ;

Lin, JYC ;

Chen, ST ;

Chang, NC .

JOURNAL OF THE CHINESE CHEMICAL SOCIETY, 2002, 49 (06) :1079-1088

[8] 1,8-diazabicyclo[5.4.0]undec-7-ene:: A remarkable base in the debromination of 4-or 5-substituted N-benzyl α-bromo-α-p-toluenesulfonylglutarimide [J].

Chang, MY ;

Lin, JYC ;

Chen, ST ;

Chang, NC .

JOURNAL OF THE CHINESE CHEMICAL SOCIETY, 2002, 49 (06) :1015-1024

[9] A synthesis of thalidomide [J].

Chang, MY ;

Chang, CH ;

Chen, ST ;

Chang, NC .

JOURNAL OF THE CHINESE CHEMICAL SOCIETY, 2002, 49 (03) :383-385

[10] Reaction of different α-sulfonyl acetamides with methyl acrylate [J].

Chang, MY ;

Chen, ST ;

Chang, NC .

TETRAHEDRON, 2002, 58 (25) :5075-5080

← 1 2 3 4 →