通过傅克反应从呋喃高效对映选择性合成2-呋喃基羟基乙酸酯。

Highly enantioselective synthesis of 2-furanyl-hydroxyacetates from furans via the Friedel-Crafts reaction.

作者信息

Majer Jakub, Kwiatkowski Piotr, Jurczak Janusz

机构信息

Institute of Organic Chemistry, Polish Academy of Sciences, Warsaw, Poland.

出版信息

Org Lett. 2008 Jul 17;10(14):2955-8. doi: 10.1021/ol800927w. Epub 2008 Jun 24.

DOI:10.1021/ol800927w

PMID:18572948

Abstract

The Friedel-Crafts reaction of alkyl glyoxylates with variously substituted furans was found to be efficiently catalyzed under simple, undemanding conditions by a 6,6'-dibromo-BINOL/Ti(IV) complex with high enantioselectivity. The reaction afforded chiral substituted 2-furanyl-hydroxyacetic acid esters, compounds of high synthetic interest, in good yield and enantiomeric excess, in most examples in the range of 90-97%.

摘要

发现6,6'-二溴-BINOL/钛(IV)配合物在简单、无需苛刻条件下能高效催化乙醛酸烷基酯与各种取代呋喃的傅克反应，且对映选择性高。该反应以良好的产率和对映体过量得到了具有高合成价值的手性取代2-呋喃基-羟基乙酸酯，在大多数实例中，对映体过量在90%-97%范围内。