Julia-Colonna stereoselective epoxidation of some α,β-unsaturated enones possessing a stereogenic centre at the γ-position:: synthesis of a protected galactonic acid derivative

被引:18
作者
Ray, PC [1 ]
Roberts, SM [1 ]
机构
[1] Univ Liverpool, Dept Chem, Liverpool L69 7ZD, Merseyside, England
来源
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 2001年 / 02期
关键词
D O I
10.1039/b007100p
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The oxidation of enones 6-8 using peroxide or percarbonate and polyleucines as catalysts gave the corresponding diastereomers 9-12 in high yield. The compound 9 was converted into the galactonic acid derivative 16 in five steps and in an overall yield of nearly 60%. Polyleucines are shown to be catalysts powerful enough to overturn the intrinsic stereocontrol in the chosen substrates.
引用
收藏
页码:149 / 153
页数:5
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