Pinacol couplings of a series of aldehydes and ketones with SmI2/Sm/Me3SiCl in DME

TETRAHEDRON

卷:71

Article

Yoshimura, Aya¹  Saeki, Tomokazu¹  Nomoto, Akihiro¹  Ogawa, Akiya¹ 

[1] Osaka Prefecture Univ, Grad Sch Engn, Dept Appl Chem, Sakai, Osaka 5998531, Japan

关键词: Pinacol coupling;    Samarium diiodide;    Carbonyl compound;    Trimethylchlorosilane;    1,2-Dimethoxyethane;   

DOI  :  10.1016/j.tet.2015.06.007

来源: Elsevier

【 摘 要 】

The pinacol coupling is one of the most significant methods to synthesize vic-diols. The combination of samarium diiodide (SmI2) and samarium metal successfully induces the selective pinacol couplings of not only aromatic aldehydes and ketones but also aliphatic ones in the presence of trimethylchlorosilane (Me3SiCI) in 1,2-dimethoxyethane (DME). DME is the most suitable solvent for the reduction system using SmI2 and Me3SiCI. Me3SiCI, a widely available additive, prevents the decomposition of the formed vic-diols, i.e., meso-isomers, and controls their stereochemistry. In particular, the pinacol couplings of sterically hindered aliphatic aldehydes and ketones proceed with excellent diastereoselectivities to afford dl-isomers in good yields. (C) 2015 Elsevier Ltd. All rights reserved.

【 授权许可】

Free