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

2015; Elsevier BV; Volume: 71; Issue: 33 Linguagem: Inglês

10.1016/j.tet.2015.06.007

1464-5416

Aya Yoshimura, Tomokazu Saeki, Akihiro Nomoto, Akiya Ogawa,

Catalytic C–H Functionalization Methods

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 (Me3SiCl) in 1,2-dimethoxyethane (DME). DME is the most suitable solvent for the reduction system using SmI2 and Me3SiCl. Me3SiCl, 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.