四氢萘的立体选择性分子内 Frie del-Crafts 烷基化反应。

Diastereoselective intramolecular Friedel-Crafts alkylation of tetralins.

机构信息

Davenport Chemical Laboratories, Department of Chemistry, University of Toronto, 80 St George Street, Toronto, Ontario M5S 3H6, Canada.

出版信息

Org Lett. 2011 Jun 17;13(12):3000-3. doi: 10.1021/ol2008236. Epub 2011 May 18.

DOI:10.1021/ol2008236

PMID:21591612

Abstract

An efficient and versatile synthesis of cis-hexahydrobenzophenanthridines starting from readily available tetralins has been developed using an intramolecular Friedel-Crafts alkylation as a key step. The substrates were prepared via a highly stereocontrolled rhodium-catalyzed ring-opening reaction of meso-oxabicyclic alkenes and a hydrogenation sequence. Thus, a wide variety of complex tetracyclic compounds have been isolated with a high level of regio-, diastereo-, and enantioselectivity.

摘要

已经开发出一种从易得的四氢萘出发，通过分子内傅克烷基化反应作为关键步骤，高效且多功能的合成顺式六氢苯并菲啶的方法。底物是通过高立体选择性的铑催化的内消旋氧杂双环烯烃的开环反应和氢化序列制备的。因此，通过该方法分离得到了多种具有高区域、非对映和对映选择性的复杂四环化合物。