Tetrahedron: Asymmetry

Synthesis and application of oxadiazines as chiral ligands for the enantioselective addition of diethylzinc to aldehydes

MA Dean, SR Hitchcock

Index: Dean, Melissa A.; Hitchcock, Shawn R. Tetrahedron Asymmetry, 2010 , vol. 21, # 20 p. 2471 - 2478

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Citation Number: 7

Abstract

A series of oxadiazines derived from l-phenylalanine bearing phenolic substituents have been synthesized in a multistep, one pot process. This process involves the reaction of a mixed anhydride with a β-hydrazino alcohol, methanesulfonylation of the alcohol moiety, and base induced cyclization. The resultant oxadiazines were employed in the asymmetric addition of diethylzinc to aldehydes.