Enantioselective Synthesis of (-)-(7a S)-2,3,7,7a-Tetrahydro-7a- phenylthio-1 H -indene-1,5(6 H)-dione and (+)-(8a S)-3,4,8,8a-Tetrahydro-8a-phenylthio-1,6(2 H,7 H)-naphthalenedione

Stefan Kwiatkowski, Ashfaq Syed, Carolyn P. Brock, David S. Watt

Research output: Contribution to journalArticlepeer-review

24 Scopus citations

Abstract

Application of the Hajos-Parrish asymetrically biased aldol condensation to 2-(3-oxobutyl)-2-phenylthio-1,3-cyclopentanedione (5a) or 2-(3-oxobutyl) -2-phenylthio-1,3-cyclohexanedione (5b) using (R)-(+)-proline provided (-)-(7aS)-2,3,7,7a-tetrahydro-7a-phenylthio-1H-indene -1,5(6H)-dione (7a) and (+)-(8aS)-3,4,8,8a-tetrahydro-8a -phenylthio-1,6(2H,7H)-naphthalenedione (7b), respectively, in = 95% enantiomeric excess, as determined by 1H-NMR analysis using tris[3-heptafluoropropylhydroxymethylene)-(+)-camphorato]europium(III).

Original languageEnglish
Pages (from-to)818-820
Number of pages3
JournalSynthesis
Volume1989
Issue number11
DOIs
StatePublished - 1989

Bibliographical note

Publisher Copyright:
© 1989 Georg Thieme Verlag. All rights reserved.

ASJC Scopus subject areas

  • Catalysis
  • Organic Chemistry

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