RING CONTRACTION OF 2-O-TRIFLUOROMETHANESULFONATES OF ALPHA-HYDROXY-GAMMA-LACTONES TO OXETANE CARBOXYLIC ESTERS

被引：40
|
作者：
WITTY, DR
FLEET, GWJ
VOGT, K
WILSON, FX
WANG, Y
STORER, R
MYERS, PL
WALLIS, CJ
机构：
[1] UNIV OXFORD,DYSON PERRINS LAB,S PARKS RD,OXFORD OX1 3QY,ENGLAND
[2] GLAXO GRP RES LTD,WARE SG12 0DP,HERTS,ENGLAND
[3] GLAXO GRP RES LTD,GREENFORD UB6 0HE,MIDDX,ENGLAND
来源：
TETRAHEDRON LETTERS | 1990年 / 31卷 / 33期
关键词：
D O I：
10.1016/S0040-4039(00)97734-7
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
2-O-Trifluoromethanesulphonate esters of the four diastereomeric 3,5-di-O-benzyl-pentono-1,4-1actones gave, on treatment with potassium carbonate in methanol, efficient ring contraction to methyl oxetane-2-carboxylic esters. The stereochemistry at C-2 of the resulting oxetanes is determined largely by the configuration at C-3, rather than C-2, of the lactone. © 1990.
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页码：4787 / 4790
页数：4
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