Synthesis of optically active thiadecalins and thiahydrindans by a proline-catalyzed intramolecular Michael reaction

A. P. Kozikowski, B. B. Mugrage

Research output: Contribution to journalArticle

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
StatePublished - 1989
Externally publishedYes

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Enantiomers
Crystallization
Proline
Yeast
thiopyran

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Synthesis of optically active thiadecalins and thiahydrindans by a proline-catalyzed intramolecular Michael reaction. / Kozikowski, A. P.; Mugrage, B. B.

In: Journal of Organic Chemistry, Vol. 54, No. 10, 1989, p. 2274-2275.

Research output: Contribution to journalArticle

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