AN IMPROVED SYNTHESIS AND RESOLUTION OF (+/-)-CIS,CIS-SPIRO[4.4]NONANE-1,6-DIOL

被引:50
作者
NIEMAN, JA [1 ]
PARVEZ, M [1 ]
KEAY, BA [1 ]
机构
[1] UNIV CALGARY,DEPT CHEM,CALGARY T2N 1N4,ALBERTA,CANADA
关键词
D O I
10.1016/S0957-4166(00)82242-9
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
(+/-)-cis,cis-Spiro[4.4]nonane-1,6-diol (2) is synthesized stereoselectively in four steps (51%) beginning with ethyl 2-oxocyclopentanecarboxylate. An improved resolution of diol 2 is described by preparing diastereomeric ketals of (1R)-(+)-camphor. The relative stereochemistry of cis,cis-diol 2 is unambiguously assigned via an X-ray crystal structure of the bis-(p-nitrobenzoate) derivative.
引用
收藏
页码:1973 / 1976
页数:4
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