Ethyl N-Boc- and N-Z-α-tosylglycinates, which were readily available from t-butyl or benzyl carbamate, ethyl glyoxylate, and sodium p-toluenesulfinate in formic acid, were reacted with a variety of nitro compounds in the presence of a base to afford the corresponding α,β-didehydroamino acid derivatives in good yields. Eventually, it was found that the (Z)-isomer was predominantly formed in the present method.

Ethyl N-Boc- and N-Z-α-tosylglycinates were reacted with a variety of aldehydes in the presence of tributylphosphine and a base to afford the corresponding α,β-didehydroamino acid derivatives with high (Z)-selectivity in good yields. Moreover, ethyl (4S)- and (4R)-2-(N-Boc-amino)-4,5-isopropylidenedioxy-2-pentenoates prepared by the present method were converted to (2S, 4S)- and (2R, 4R)-4-hydroxyprolines, respectively.

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