AN IMPROVED REACTION OF TRIS(METHYLTHIO)METHANE WITH EPOXIDES - APPLICATION TO THE EFFICIENT SYNTHESIS OF BETA-HYDROXY ESTERS

被引:8
作者
ABOOD, NA
机构
[1] Department of Chemistry, Searle Research and Development, Skokie, Illinois
关键词
D O I
10.1080/00397919308009842
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Tris(methylthio)methyllithium reacts efficiently with epoxides in THF:HMPA (5:1) at low temperature to give beta-hydroxy orthotrithiocarboxylates which are converted to beta-hydroxy esters in high yield.
引用
收藏
页码:811 / 815
页数:5
相关论文
共 6 条
[1]   OXIDATIVE HYDROLYSIS OF 1,3-DITHIANE DERIVATIVES TO CARBONYL COMPOUNDS USING N-HALOSUCCINIMIDE REAGENTS [J].
COREY, EJ ;
ERICKSON, BW .
JOURNAL OF ORGANIC CHEMISTRY, 1971, 36 (23) :3553-&
[2]  
Damon R.E., 1976, TETRAHEDRON LETT, V19, P1561
[3]  
GROBEL BT, 1977, SYNTHESIS-STUTTGART, P357
[4]   METALATED ORTHOTHIOFORMATES [J].
SEEBACH, D .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1967, 6 (05) :442-&
[5]   TRIS(PHENYLTHIO)METHYLLITHIUM - UNUSUAL CARBENOID [J].
SEEBACH, D .
CHEMISCHE BERICHTE-RECUEIL, 1972, 105 (02) :487-&
[6]   STUDIES ON THE SYNTHESES OF THE APLYSIATOXINS - SYNTHESIS OF A SELECTIVELY-PROTECTED FORM OF THE C-27-C-30 (DIHYDROXYBUTANOATE) MOIETY OF OSCILLATOXIN-A [J].
WALKUP, RD ;
CUNNINGHAM, RT .
TETRAHEDRON LETTERS, 1987, 28 (35) :4019-4022