Photo aldol reactions with 5-methoxyoxazoles: Highly regio-and diastereoselective synthesis of α-amino β-hydroxy carboxylic acid derivatives

AG Griesbeck, S Bondock

Index: Griesbeck, Axel G.; Bondock, Samir Canadian Journal of Chemistry, 2003 , vol. 81, # 6 p. 555 - 559

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Citation Number: 12

Abstract

A versatile route to derivatives of α-amino β-hydroxy carboxylic acids, either with tertiary (from a corresponding glycine equivalent) or a quaternary α-carbon center is described. The key reaction is the cycloaddition of electronically excited carbonyl compounds (aromatic and aliphatic aldehydes, respectively) to oxazoles. To make the products hydrolytically more labile, a methoxy substituent at position C-5 was introduced leading to the formation of ...