Tetrahedron: Asymmetry

(R)-and (S)-3-hydroxy-4, 4-dimethyl-1-phenyl-2-pyrrolidinone as chiral auxiliaries for the asymmetric synthesis of α-hydroxy acids

P Camps, F Pérez, N Soldevilla

Index: Camps, Pelayo; Perez, Francesc; Soldevilla, Nuria Tetrahedron Asymmetry, 1997 , vol. 8, # 11 p. 1877 - 1894

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Citation Number: 36

Abstract

Rac-α-bromo acids, rac-4, have been converted into (R)-or (S)-α-hydroxy acid,(R)-or (S)-9, by DCC-induced esterification with the chiral auxiliaries (R)-or (S)-1, followed by reaction with sodium p-methoxyphenoxide in the presence of tetra-n-hexylammonium iodide, conditions of dynamic kinetic resolution, to give quite diastereoselectively the (αR, 3S)-or (αS, 3R)-α-(p-methoxyphenoxy) esters, 7, which were then oxidized with ceric ammonium ...