Michael additions catalysed by cinchona alkaloids bound via their vinyl groups to preformed crosslinked polymers

Philip Hodge*, Ezzatollah Khoshdel, Janette Waterhouse, Jean M.J. Fréchet

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

51 Scopus citations

Abstract

Cinchona alkaloids have been satisfactorily bound via their vinyl groups to crosslinked polymers containing thiol residues. The products have been used to catalyse one or more of the following Michael additions: the additions of (1) thio-p-cresol, (2) p-chlorothiophenol, and (3) thiobenzoic acid to cyclohex-2-en-1-one, and (4) of toluene-α-thiol to 2-nitrostyrene. The steric course of reactions (1) - (3) is dominated by the configurations of C-8 and C-9 in the alkaloids, but the nature of the C-3 group does have an effect and this probably explains why the optical yields obtained using the polymer-supported catalysts were lower than those obtained using the free alkaloids. The optical yields obtained in reaction (4), though small, did not follow this pattern. The polymers afforded higher optical yields than the free alkaloids and, in one case, the predominant enantiomer was of opposite configuration.

Original languageEnglish (US)
Pages (from-to)2327-2331
Number of pages5
JournalJournal of the Chemical Society, Perkin Transactions 1
StatePublished - 1985
Externally publishedYes

ASJC Scopus subject areas

  • Chemistry(all)

Fingerprint Dive into the research topics of 'Michael additions catalysed by cinchona alkaloids bound via their vinyl groups to preformed crosslinked polymers'. Together they form a unique fingerprint.

Cite this