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Photocycloaddition of 5-methoxyoxazoles to aldehydes and alpha-keto esters: A comprehensive view on stereoselectivity, triplet biradical conformations, and synthetic applications of paterno-buchi adducts
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Photocycloaddition of 5-methoxyoxazoles to aldehydes and alpha-keto esters: A comprehensive view on stereoselectivity, triplet biradical conformations, and synthetic applications of paterno-buchi adducts

Axel G. Griesbeck and Samir Bondock
Australian journal of chemistry, Vol.61(8), pp.573-580
15/08/2008

Abstract

Chemistry Chemistry, Multidisciplinary Physical Sciences Science & Technology
The photocycloaddition of carbonyl compounds ( aldehydes and keto esters, respectively) with 5-methoxyoxazoles bearing substituents at C2 and C4 is described with respect to regio-and diastereoselectivity. In all cases the reactions proceed with excellent regioselectivity and with high to moderate (exo) diastereoselectivity independent of the nature of the excited carbonyl compound. The products can be easily ring-opened to give alpha-amino, beta-hydroxy carboxylic acid derivatives.

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