A C-H oxidation approach for streamlining synthesis of chiral polyoxygenated motifs

TETRAHEDRON

卷:69

Article

Covell, Dustin J.¹  White, M. Christina² 

[1] Univ Penn, Dept Pathol & Lab Med, Sch Med, Philadelphia, PA 19104 USA

[2] Univ Illinois, Dept Chem, Roger Adams Lab, Urbana, IL 61801 USA

关键词: C-H oxidation;    Allylic oxidation;    Allylic alcohols;    Enantioselective;    Palladium;    Sulfoxide;   

DOI  :  10.1016/j.tet.2013.05.012

来源: Elsevier

【 摘 要 】

Chiral oxygenated molecules are pervasive in natural products and medicinal agents; however, their chemical syntheses often necessitate numerous, wasteful steps involving functional group and oxidation state manipulations. Herein a strategy for synthesizing a readily diversifiable class of chiral building blocks, allylic alcohols, through sequential asymmetric C H activation/resolution is evaluated against the state-of-the-art. The C H oxidation routes' capacity to strategically introduce oxygen into a sequence and thereby minimize non-productive manipulations is demonstrated to effect significant decreases in overall step-count and increases in yield and synthetic flexibility. (C) 2013 Elsevier Ltd. All rights reserved.

【 授权许可】

Free