Phosphazene-catalyzed desymmetrization of cyclohexadienones by dithiane addition

Beilstein Journal of Organic Chemistry

Matthew A. Horwitz¹  Jeffrey S. Johnson¹  Elisabetta Massolo¹ 

[1] Department of Chemistry, University of North Carolina at Chapel Hill, Chapel Hill, NC 27599-3290, USA;

关键词: conjugate addition;    cyclohexadienones;    dearomatization;    desymmetrization;    dithiane;    iminophosphoranes;    organocatalysis;    phosphazenes;   

DOI  :  10.3762/bjoc.13.75

来源: DOAJ

【 摘 要 】

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.

【 授权许可】

Unknown