We have recently developed a novel synthetic method for �-amino-a-hydroxy acids via the tandem reactions between phenylsulfonylnitromethane and stable a-amino aldehydes with the N-tethered hydroxymethyl group. Without any of chiral catalysts or chiral auxiliaries, high stereoselectivity (more than 20:1) for threo-�-amino-a-hydroxy acid has been observed by the three sequential reactions (the nitro-aldol, the elimination, and the conjugate addition) followed by the in-situ oxidation.Here, an application of the synthetic protocol developed as the above will be reported for the synthesis of threo-�-benzyloxyaspartate (TBOA). Although TBOA has been known as an important inhibitor of neuronal excitatory glutamate transporters in the brain, only a few stereoselective synthetic methods have been reported. Thus, the reaction of a D-serinal derivative with phenylsulfonylnitromethane introduced the required a-hydroxy group of TBOA with a high stereoselectivity and the following oxidation reactions of the key intermediate gave all the functional groups present in TBOA in an efficient manner.

Application of the <i>N</i>-hydroxymethyl group for the synthesis of �-amino-a-hydroxy acids: <i>threo</i>-�-benzyloxyaspartate

247th National Meeting (2014)

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Application of the N-hydroxymethyl group for the synthesis of �-amino-a-hydroxy acids: threo-�-benzyloxyaspartate