A New Synthetic Method for the Preparation of. ALPHA.,. BETA.-Didehydroamino Acid Derivatives by Means of a Wittig-Type Reaction. Syntheses of (2S, 4S)-and (2R, …

R Kimura, T Nagano, H Kinoshita

Index: Kimura, Rumi; Nagano, Tanemasa; Kinoshita, Hideki Bulletin of the Chemical Society of Japan, 2002 , vol. 75, # 11 p. 2517 - 2525

Full Text: HTML

Citation Number: 27

Abstract

Ethyl N-Boc-and NZ-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.