Macrocycles Derived from Cinchona Alkaloids: A Thermodynamic vs Kinetic Study

Stuart J. Rowan, Jeremy K M Sanders

Research output: Contribution to journalArticle

67 Citations (Scopus)

Abstract

Cyclization of the quinine-derived monomer (2a): HO-Cq-OMe, under thermodynamic control, gives mainly cyclic trimer Cq3 (7a), whereas kinetic cyclization of the similar monomer HO-Cq-OH (8) gives a mixture of cyclic products. This difference in product distribution is attributed to predisposition of the monomer unit, which means the building block adopts a more stable conformation in cyclic trimer than it can in cyclic tetramer. The reversibility of the thermodynamic reaction was demonstrated using electrospray mass spectrometry to monitor the catalyzed mixing of the two cyclic trimers Cq3 (7a) and Cc3 (7b), which results in the statistically expected 1:3:3:1 ratio of all possible cyclic trimers Cc3:Cc2Cq:CcCq2:Cq3.

Original languageEnglish
Pages (from-to)1536-1546
Number of pages11
JournalJournal of Organic Chemistry
Volume63
Issue number5
Publication statusPublished - 1998 Mar 6
Externally publishedYes

ASJC Scopus subject areas

  • Organic Chemistry

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