Sparteine-mediated asymmetric nucleophilic substitution at prochiral, sp3-hybridized carbon

被引：11
|
作者：
Muller, P [1 ]
Nury, P [1 ]
机构：
[1] Univ Geneva, Dept Organ Chem, CH-1211 Geneva 4, Switzerland
来源：
ORGANIC LETTERS | 2000年 / 2卷 / 18期
关键词：
D O I：
10.1021/ol0062749
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
2-Phenyl-1,3-dioxolanes (1) react with organolithium reagents (2), associated with (-)-sparteine, in the presence of BF3. OEt2 to afford chiral monosubstitution products 3, Enantioselectivity is highest if both 1 and 2 carry alkyl substituents in the ortho position. However, the enantioselectivity decreases in the case of very bulky substituents such as tert-butyl or phenyl.
引用
收藏
页码：2845 / 2847
页数：3
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