Tetrahedron Asymmetry p. 1227 - 1234 (1996)
Update date:2022-09-26
Topics:
Camps, Pelayo
Gimenez, Silvia
Reaction of rac-α-substituted arylacetyl chlorides with (R)- and (S)-3-hydroxy-4,4-dimethyl-1-phenyl-2-pyrrolidinone under standard esterification conditions, gave esters (3R,αR)- and (3S,αS)-3, respectively, with a diastereoselectivity which diminishes on increasing the steric effect of the α-substituent. Controlled acidic hydrolysis of esters 3 afforded the corresponding acids 4 with minimal racemization. Boron tribromide demethylation of (R)- and (S)-4d gave without racemization the hydroxyacids (R)- and (S)-4e, known precursors of (R)- and (S)-iodoalphionic acid.
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