Asymmetric allylation of aldehydes with etherification by allyltrimethylsilane promoted by chiral alcohol modified aluminum reagents

被引：2
|
作者：
Yang, Y [1 ]
Wang, D [1 ]
机构：
[1] Chinese Acad Sci, Inst Chem, Beijing 100080, Peoples R China
来源：
PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS | 1998年 / 139卷
基金：
中国国家自然科学基金;
关键词：
allyltrimethylsilane; asymmetric allylation; homoallylic ether; chiral alcohol; chirally modified aluminum reagent;
D O I：
10.1080/10426509808035688
中图分类号：
O61 [无机化学];
学科分类号：
070301 ; 081704 ;
摘要：
Leiws acid AlCl3 was modified by chiral alcohols, forming chiral aluminum reagents (*ROH/AlCl3). *ROH/AlCl3 was used to promote asymmetric allylation of aldehydes with etherification by allyltrimethylsilane, giving the chiral homoallylic ethers in good yields and good to excellent de (51-93%). The monoalkoxy aluminum (*RO)AlCl2 generated in situ was determined as an active and stereogenic species in one pot allylation reaction of aldehyde. The turnover of diastereoselectivity with the ratio of menthol to AlCl3 was observed. Two different hemiacetal intermediates were suggested.
引用
收藏
页码：193 / 207
页数：15
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