Stereoselective VO(acac)2 catalyzed epoxidation of acyclic homoallylic diols. Complementary preparation of C2-syn-3,4-epoxy alcohols

TETRAHEDRON

卷:67

Article

Rodriguez-Berrios, Raul R.¹  Torres, Gerardo¹  Prieto, Jose A.¹ 

[1] Univ Puerto Rico, Dept Chem, San Juan, PR 00931 USA

关键词: Epoxidation;    Homoallylic alcohols;    Polypropionates;    VO(acac)(2);   

DOI  :  10.1016/j.tet.2010.11.079

来源: Elsevier

【 摘 要 】

A substrate-controlled stereoselective epoxidation of free and monoprotected homoallylic diols was developed. This second-generation approach is based on the incorporation of a primary hydroxy directing group at the C2 methyl carbon, which changes the nature of the vanadium ester intermediate providing a new diastereoselectivity manifold for the preparation of 3,4-epoxy alcohols. This modification favored the formation of the challenging C2-syn epoxy alcohol product not previously available using the standard homoallylic alcohol substrates. These new epoxy alcohol diastereomers expand the scope and generality for the utilization of 3,4-epoxy alcohols as precursors for stereoselective polypropionate synthesis. (C) 2010 Elsevier Ltd. All rights reserved.

【 授权许可】

Free