Preparation of enantiomerically pure protected 4-oxo. alpha.-amino acids and 3-aryl. alpha.-amino acids from serine

…, N Wishart, A Wood, K James, MJ Wythes

Index: Jackson, Richard F. W.; Wishart, Neil; Wood, Anthony; James, Keith; Wythes, Martin J. Journal of Organic Chemistry, 1992 , vol. 57, # 12 p. 3397 - 3404

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Citation Number: 178

Abstract

Important goals for such investigations are the development of synthetic equivalents for the alanine@-cation 1 and the alanine@-anion 2. There are several approaches to the synthon 1, including 3-iodo-and 3-(tosyloxy) alanhe derivatives 3a and 3b, 4 the &lactone 4, 5 the aziridine 5: and the sulfamidate 6,'all of which are derived from serine. In addition, an indirect approach using the D-mannitolderived bis (aziridine) 7 has also been explored? ...