BETA,GAMMA-EPOXY SULFONES IN ORGANIC-SYNTHESIS .2. PREPARATION OF BETA,GAMMA-BIFUNCTIONALIZED SULFONES

被引：28

作者：

NAJERA, C

SANSANO, JM

机构：

[1] Departamento de Química Orgánica, Facultad de Ciencias, Universidad de Alicante

来源：

TETRAHEDRON | 1991年 / 47卷 / 28期

关键词：

D O I：

10.1016/S0040-4020(01)87131-3

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Heteronucleophiles reagents react with beta,gamma-epoxy sulfones 1 at the gamma-position in the presence of Ti(OPr(i))4 or magnesium halides to afford regioselectively gamma-functionalized beta-hydroxy sulfones 2. With soft nucleofiles such as sodium azide, triphenylphosphine, or sodium benzethiolate the reaction takes place in the absence of Lewis acids. In the case of basic reagents such as sodium methoxide or diethylamine the corresponding regioisomers, the beta-functionalized gamma-hydroxy sulfones 3 were exclusively obtained. The preparation of compounds 3 (R2 = H) was also carried out starting from 3-tosyl-2-propen-1-ol (4) by Micheal addition of different heteronucleophiles.

引用

页码：5193 / 5202

页数：10

共 17 条

[1] MILD AND STEREOCONTROLLED SYNTHESIS OF IODOHYDRINS AND BROMOHYDRINS BY X2-TI(O-ISO-PR)4 OPENING OF EPOXY ALCOHOLS [J].