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Phosphazene-catalyzed desymmetrization of cyclohexadienones by dithiane addition.

ABSTRACT: 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.

SUBMITTER: Horwitz MA

PROVIDER: S-EPMC5433211 | biostudies-literature | 2017

REPOSITORIES: biostudies-literature

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Phosphazene-catalyzed desymmetrization of cyclohexadienones by dithiane addition.

Horwitz Matthew A MA Massolo Elisabetta E Johnson Jeffrey S JS

Beilstein journal of organic chemistry 20170424

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. ...[more]

PMID: 28546832

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