Report

Diels-Alder in Aqueous Molecular Hosts: Unusual Regioselectivity and Efficient Catalysis

Science  14 Apr 2006:
Vol. 312, Issue 5771, pp. 251-254
DOI: 10.1126/science.1124985

You are currently viewing the abstract.

View Full Text

Via your Institution

Log in through your institution

Log in through your institution


This article has a correction. Please see:

Abstract

Self-assembled, hollow molecular structures are appealing as synthetic hosts for mediating chemical reactions. However, product binding has inhibited catalytic turnover in such systems, and selectivity has rarely approached the levels observed in more structurally elaborate natural enzymes. We found that an aqueous organopalladium cage induces highly unusual regioselectivity in the Diels-Alder coupling of anthracene and phthalimide guests, promoting reaction at a terminal rather than central anthracene ring. Moreover, a similar bowl-shaped host attains efficient catalytic turnover in coupling the same substrates (although with the conventional regiochemistry), most likely because the product geometry inhibits the aromatic stacking interactions that attract the planar reagents to the host.

View Full Text

Related Content