Diels-alder in aqueous molecular hosts: Unusual regioselectivity and efficient catalysis

Michito Yoshizawa, Masazumi Tamura, Makoto Fujita

Research output: Contribution to journalArticlepeer-review

869 Citations (Scopus)

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.

Original languageEnglish
Pages (from-to)251-254
Number of pages4
JournalScience
Volume312
Issue number5771
DOIs
Publication statusPublished - 2006 Apr 14
Externally publishedYes

ASJC Scopus subject areas

  • General

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