Phosphazene-catalyzed desymmetrization of cyclohexadienones by dithiane addition

Matthew A. Horwitz; Elisabetta Massolo; Jeffrey S. Johnson

doi:10.3762/bjoc.13.75

Beilstein Journal of Organic Chemistry (Apr 2017)

Phosphazene-catalyzed desymmetrization of cyclohexadienones by dithiane addition

Matthew A. Horwitz,
Elisabetta Massolo,
Jeffrey S. Johnson

Affiliations

Matthew A. Horwitz: Department of Chemistry, University of North Carolina at Chapel Hill, Chapel Hill, NC 27599-3290, USA
Elisabetta Massolo: Department of Chemistry, University of North Carolina at Chapel Hill, Chapel Hill, NC 27599-3290, USA
Jeffrey S. Johnson: Department of Chemistry, University of North Carolina at Chapel Hill, Chapel Hill, NC 27599-3290, USA

DOI: https://doi.org/10.3762/bjoc.13.75
Journal volume & issue: Vol. 13, no. 1
pp. 762 – 767

Abstract

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We report a desymmetrization of cyclohexadienones by intramolecular conjugate addition of a tethered dithiane nucleophile. Mild reaction conditions allow the formation of diversely functionalized fused bicyclic lactones. The products participate in facially selective additions from the convex surface, leading to allylic alcohol derivatives.

Published in Beilstein Journal of Organic Chemistry

ISSN: 1860-5397 (Online)
Publisher: Beilstein-Institut
Country of publisher: Germany
LCC subjects: Science: Chemistry: Organic chemistry
Website: http://www.beilstein-journals.org/bjoc

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