Journal of Organic Chemistry 2003-10-31

Synthesis of cyclic and acyclic beta-amino acids via chelation-controlled 1,3-dipolar cycloaddition.

Roger Hanselmann, Jiacheng Zhou, Philip Ma, Pat N Confalone

Index: J. Org. Chem. 68(22) , 8739-41, (2003)

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Abstract

Isoxazolidines have been synthesized in diastereomeric excess up to 94% via a MgBr2-induced chelation-controlled 1,3-dipolar cycloaddition reaction with N-hydroxyphenylglycinol as a chiral auxiliary. The diastereomerically pure isoxazolidines were further transformed into cyclic and acyclic beta-amino acid derivatives.