Synthesis of e rythro-α-Amino β-hydroxy Carboxylic Acid Esters by Diastereoselective Photocycloaddition of 5-Methoxyoxazoles with Aldehydes

AG Griesbeck, S Bondock, J Lex

Index: Griesbeck, Axel G.; Bondock, Samir; Lex, Johann Journal of Organic Chemistry, 2003 , vol. 68, # 26 p. 9899 - 9906

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Citation Number: 45

Abstract

A new photoa ldol route to α-amino-β-hydroxy carboxylic acid esters is initiated by the photocycloaddition of aromatic or aliphatic aldehydes to 5-methoxyoxazoles. The 4- unsubstituted 5-methyloxazole 1 gave the cycloadducts 8a-f in high yields and excellent exo- diastereoselectivities. Hydrolysis of 8a-f gives the N-acetyl α-amino-β-hydroxy esters 9a-f, which could be subsequently converted into the corresponding Z-didehydro α-amino ...