ON THE COUPLING REACTION OF 1-BENZOTHIAZOLYL-2-AZA-PENTADIENYL METALS WITH C-ELECTROPHILES

被引：3

作者：

EPIFANI, E

FLORIO, S

PERRONE, D

VALLE, G

机构：

[1] UNIV BARI,FAC FARM,DIPARTIMENTO FARMACO CHIM,I-70124 BARI,ITALY

[2] UNIV PADUA,CTR STUDIO BIOPOLIMERI,I-35100 PADUA,ITALY

来源：

TETRAHEDRON | 1991年 / 47卷 / 25期

关键词：

D O I：

10.1016/S0040-4020(01)87115-5

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The coupling reaction of 1-benzothiazolyl-2-aza-pentadienyl metals 3 with carbonyl compounds has been investigated. The reaction of 3 with aldehydes leads to alpha and/or gamma-regioisomeric homoallylic alcohols 8, 9 and 10 depending upon the experimental conditions. The coupling of 3 with alpha, beta-unsaturated carbonyl compounds was highly alpha-1, 4-regioselective. The reaction of 3b and 3e with chalcone afforded small amount of pyrrolidine 13, while the coupling of 3b and 3c with 2-cyclopentenone provided mainly pyrrolidines 18a and 18b respectively.

引用

页码：4465 / 4476

页数：12

共 13 条

[1] GENERAL REACTIVITY OF 2-LITHIOBENZOTHIAZOLE TO VARIOUS ELECTROPHILES AND THE USE AS A FORMYL ANION EQUIVALENT IN THE SYNTHESIS OF ALPHA-HYDROXY CARBONYL-COMPOUNDS [J].