Abstract
The selective reduction of dimethyl 3-oxoglutarate was accomplished in different levels. A high yielding sodium borohydride reduction of the keto group is fully described leading to dimethyl 3-hydroxyglutarate. When borane-dimethyl sulfide (BMS) complex was used, a diol or a triol compound can be obtained by selective or total reduction of 3-hydroxy- or 3-oxoglutarate, respectively, allowing an efficient and practical route to 1,3,5-oxygenated compounds.
Highlights
Selectivity is imperative in modern organic synthesis, especially when multifunctional molecules are involved
Our investigation began by exploring the chemoselective reduction of commercially available dimethyl 3-oxoglutarate (1) with NaBH
A chemoselective reduction to alcohol 2 was achieved in high yield (96%) and was fully described, while diol 3 was obtained in 80% yield from 2, allowing a fast access to this important oxygenated synthon
Summary
Selectivity is imperative in modern organic synthesis, especially when multifunctional molecules are involved. The reagents and conditions employed for a chemical transformation must not affect other functional groups in the molecule, leading only to the required transformation. Reductions play an important role.[1] Those transformations are known by their chemocompatibility, possibility of partial reduction, and regio- and stereoselectivity altered or controlled by neighboring groups, besides asymmetric transformations In this context, the selective reduction of dimethyl 3-oxoglutarate (1) to prepare dimethyl 3-hydroxyglutarate (2), diol 3 and triol 4 derivatives is an important approach in organic synthesis since these structures are useful intermediates in the preparation of complex molecules.[2] A
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