手性螺旋硅纳米粒子拆分芳香族醇的对映体。

Optical resolution of aromatic alcohols using silica nanoparticles grafted with helicene.

机构信息

Department of Organic Chemistry, Graduate School of Pharmaceutical Sciences, Tohoku University, Aoba, Sendai 980-8578, Japan.

出版信息

Org Lett. 2012 Jun 15;14(12):3123-5. doi: 10.1021/ol301206r. Epub 2012 May 23.

DOI:10.1021/ol301206r

PMID:22621331

Abstract

Optically active silica nanoparticles, with a 70-nm diameter, grafted with (P)-1,12-dimethyl-8-methoxycarbonylbenzo[c]phenanthrene-5-carboxyamide were synthesized, and their use in the kinetic resolution of aromatic alcohols was examined. Up to 61% ee for (S)-2,2-dimethyl-1-phenyl-1-propanol was obtained by a preferential precipitation of aggregates formed with (P)-nanoparticles.

摘要

合成了具有 70nm 直径的手性二氧化硅纳米粒子，并将其与（P）-1,12-二甲基-8-甲氧羰基苯并[c]菲啶-5-羧酰胺接枝。考察了它们在手性芳香醇动力学拆分中的应用。通过优先沉淀（P）-纳米粒子形成的聚集体，获得了（S）-2,2-二甲基-1-苯基-1-丙醇的高达 61%ee。