89525-13-3Relevant academic research and scientific papers
A new synthetic method for the preparation of α,β-didehydroamino acid derivatives by means of a wittig-type reaction. Syntheses of (2S, 4S)- and (2R, 4R)-4-hydroxyprolines
Kimura, Rumi,Nagano, Tanemasa,Kinoshita, Hideki
, p. 2517 - 2525 (2007/10/03)
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.
A new and convenient method for the synthesis of dehydroamino acids starting from ethyl N-Boc- and N-Z-α-tosylglycinates and various nitro compounds
Nagano, Tanemasa,Kinoshita, Hideki
, p. 1605 - 1613 (2007/10/03)
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.
Horner Synthesis of Didehydroamino Acid Derivatives in a Liquid-Liquid Two-Phase System
Ciattini, Pier Giuseppe,Morera, Enrico,Ortar, Giorgio
, p. 140 - 142 (2007/10/02)
Horner olefination of aldehydes 1 with N-acyl-2-(diethoxyphosphoryl)glycin ethyl esters 2 to give didehydroamino acid derivatives 3 can be performed advantageously in a 20percent aqueous sodium hydroxide/dichloromethane two-phase system in the absence of any typical phase-transfer catalyst.
