在无溶剂条件下，芳醚与三氟丙酮酸的催化及高对映选择性傅克烷基化反应。

Catalytic and highly enantioselective Friedel-Crafts alkylation of aromatic ethers with trifluoropyruvate under solvent-free conditions.

作者信息

Zhao Jun-Ling, Liu Li, Sui Yong, Liu Yu-Liang, Wang Dong, Chen Yong-Jun

机构信息

Center for Molecular Science, Institute of Chemistry, Chinese Academy of Sciences, Beijing 100080, China.

出版信息

Org Lett. 2006 Dec 21;8(26):6127-30. doi: 10.1021/ol0626037.

DOI:10.1021/ol0626037

PMID:17165946

Abstract

[Structure: see text] Highly enantioselective Friedel-Crafts alkylation of simple and aromatic ethers (4a-l) with 3,3,3-trifluoropyruvate (3) was accomplished by using chiral (4R,5S)-DiPh-BOX(1b)-Cu(OTf)2 complex (1 mol %) as a catalyst under solvent-free conditions. Excellent yields and enantioselectivities (90-93% ee, after recrystallization up to 99% ee) of the Friedel-Crafts alkylation products were obtained.

摘要

[结构：见正文] 在无溶剂条件下，以手性(4R,5S)-二苯基-BOX(1b)-Cu(OTf)₂络合物（1摩尔%）为催化剂，实现了简单醚和芳香醚(4a - l)与3,3,3 - 三氟丙酮酸(3)的高度对映选择性傅克烷基化反应。得到了高产率和对映选择性的傅克烷基化产物（产率90 - 93% ee，重结晶后高达99% ee）。