Palladium-catalyzed borylation and Suzuki coupling (BSC) to obtain β-substituted dehydroamino acid derivatives

被引：13

作者：

Abreu, AS ^{[1
]}

Silva, NO ^{[1
]}

Ferreira, PMT ^{[1
]}

Queiroz, MJRP ^{[1
]}

机构：

[1] Univ Minho, Dept Quim, P-4710057 Braga, Portugal

来源：

TETRAHEDRON LETTERS | 2003年 / 44卷 / 32期

关键词：

benzo[b]thiophenes; borylation; palladium; Suzuki coupling; dehydroamino acids;

D O I：

10.1016/S0040-4039(03)01473-4

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Several benzo[b]thienyidehydroamino acids were prepared by one-pot palladium-catalyzed borylation and Suzuki coupling (BSC) from bromobenzo[b]thiophenes containing EDG (OMe or Me), as the component to be borylated with pinacolborane, and pure stereoisomers of beta-bromodehydroamino acid derivatives. To our knowledge it is the first time that the BSC reaction involves a non aromatic system. (C) 2003 Elsevier Ltd. All rights reserved.

引用

收藏

页码：6007 / 6009

页数：3

相关论文

共 10 条

[1] Synthesis of novel amino acids and dehydroamino acids containing the benzo[b]thiophene moiety [J].

Abreu, AS ;

Silva, NO ;

Ferreira, PMT ;

Queiroz, MJRP .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2003, 2003 (08) :1537-1544

[2] Palladium-catalyzed borylation of ortho-substituted phenyl halides and application to the one-pot synthesis of 2,2′-disubstituted biphenyls [J].

Baudoin, O ;

Guénard, D ;

Guéritte, F .

JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (26) :9268-9271

[3] Application of the palladium-catalyzed borylation/Suzuki coupling (BSC) reaction to the synthesis of biologically active biaryl lactams [J].

Baudoin, O ;

Cesario, M ;

Guénard, D ;

Guéritte, F .

JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (04) :1199-1207

[4] Tandem palladium-catalyzed borylation and Suzuki coupling (BSC) to thienocarbazole precursors [J].

Ferreira, ICFR ;

Queiroz, MJRP ;

Kirsch, G .

TETRAHEDRON LETTERS, 2003, 44 (23) :4327-4329

[5]

Ferreira ICFR, 2001, J HETEROCYCLIC CHEM, V38, P749

[6] Michael addition of thiols, carbon nucleophiles and amines to F17 dehydroamino acid and dehydropeptide derivatives [J].

Ferreira, PMT ;

Maia, HLS ;

Monteiro, LS ;

Sacramento, J .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2001, (23) :3167-3173

[7] Synthesis of β-substituted alanines via Michael addition of nucleophiles to dehydroalanine derivatives [J].

Ferreira, PMT ;

Maia, HLS ;

Monteiro, LS ;

Sacramento, J ;

Sebastiao, J .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2000, (19) :3317-3324

[8] Synthesis of photochromic thieno-2H-chromene derivatives [J].

Queiroz, MJRP ;

Dubest, R ;

Aubard, J ;

Faure, R ;

Guglielmetti, R .

DYES AND PIGMENTS, 2000, 47 (03) :219-229

[9]

Silva NO, 2002, EUR J ORG CHEM, V2002, P2524, DOI 10.1002/1099-0690(200208)2002:15<2524::AID-EJOC2524>3.0.CO

[10]

2-W