Synthesis of Optically Active Thiadecalins and Thiahydrindans by a Proline-Catalyzed Intramolecular Michael Reaction

A. P. Kozikowski, B. B. Mugrage

Research output: Contribution to journalLetter

Abstract

The trans-thiadecalindione 1 and the trans-and cis-thiahydrindandiones 2 and 3 were prepared from the corresponding α-thio enones 4 and 5 by a proline-catalyzed intramolecular Michael process. The optically pure enantiomers of 1 were obtained by fractional crystallization, allowing the assignment of an enantiomeric excess of 19-28% for the Michael reaction depending on reaction conditions. Additionally, thiadecalindione 1 was reduced by actively fermenting bakers' yeast to provide exclusively the product 7 resulting from reduction of the thiopyran ring carbonyl group.

Original languageEnglish (US)
Pages (from-to)2274-2275
Number of pages2
JournalJournal of Organic Chemistry
Volume54
Issue number10
DOIs
StatePublished - May 1 1989

ASJC Scopus subject areas

  • Organic Chemistry

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