External chiral ligand-induced enantioselective lithiation/SE2 reactions of isochroman and phthalan

被引：41

作者：

Tomooka, K ^{[1
]}

Wang, LF ^{[1
]}

Okazaki, F ^{[1
]}

Nakai, T ^{[1
]}

机构：

[1] Tokyo Inst Technol, Dept Chem Technol, Meguro Ku, Tokyo 1528552, Japan

来源：

TETRAHEDRON LETTERS | 2000年 / 41卷 / 32期

基金：

日本学术振兴会;

关键词：

bis(oxazoline); lithiation; isochroman; phthalan; enantioselection;

D O I：

10.1016/S0040-4039(00)01028-5

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Treatment of isochroman and phthalan with a t-BuLi/chiral bis(oxazoline) complex followed by reaction with carbon-electrophiles such as benzaldehyde and CO2 is shown to afford the a-substituted derivatives in moderate-to-high enantioselectivities (up to 97% ee and 83% ee, respectively). The asymmetric induction is proved to occur at the post-lithiation step. (C) 2000 Elsevier Science Ltd. All rights reserved.

引用

页码：6121 / 6125

页数：5

共 7 条

[1] Regioselective, diastereoselective, and enantioselective lithiation-substitution sequences: Reaction pathways and synthetic applications [J].