( R)-4-Hydroxymethyl-2-phenyl-4,5-dihydrooxazol-4-ylmethyl acetate: chiral building block for the synthesis of optically active α-substituted α-amino acid derivatives

Hiroaki Miyaoka,Makoto Yamanishi,Ayako Hoshino,Atsushi Kinbara

doi:10.1016/j.tet.2006.02.022

( R)-4-Hydroxymethyl-2-phenyl-4,5-dihydrooxazol-4-ylmethyl acetate: chiral building block for the synthesis of optically active α-substituted α-amino acid derivatives

Hiroaki Miyaoka, Makoto Yamanishi + Show 2 more

https://doi.org/10.1016/j.tet.2006.02.022

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Journal: Tetrahedron	Publication Date: Mar 10, 2006
Citations: 22

Affiliation: Tokyo University of Pharmacy and Life Sciences

#Glutamic Acid #Α-substituted Α-amino Acid + Show 8 more

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Abstract

( R)-4-Hydroxymethyl-2-phenyl-4,5-dihydrooxazol-4-ylmethyl acetate was efficiently obtained by lipase-catalyzed asymmetrization of the prochiral diol. ( R)-4-Hydroxymethyl-2-phenyl-4,5-dihydrooxazol-4-ylmethyl acetate was converted to ( R)-2-(hydroxymethyl)glutamic acid and a synthetic intermediate of (−)-deoxydysibetaine.

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