Stereoselective reduction of chiral 3-(p-tolylsulfinyl)-2-thienyl ketones. A facile entry to optically active thienylcarbinols

Article abstract of DOI:10.1248/cpb.44.1765

Stereoselective reduction of chiral 3-(p-tolylsulfinyl)-2-thienyl ketones with diisobutylaluminum hydride (DIBAL) or lithium tri-sec- butylborohydride (L-Selectride) has been achieved. Reduction of the ketones with DIBAL in the presence of a Lewis acid or with L-Selectride afforded predominantly the thienyl carbinols, while the reduction with DIBAL alone gave the other diastereoisomeric alcohols as the major product. This method has been successfully applied to an efficient route to chiral thienyl alcohols.

Full text of DOI:10.1248/cpb.44.1765

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