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Enolates derived from the N-propionoyl derivative of the "quat" chiral auxiliary (R)-(-)-5-methyl-3,3-dimethyl-2-pyrrolidinone undergo highly stereoselective aldol and alkylation reactions. Removal of the auxiliary has been demonstrated with LiOH, PhCH2OLi, MeOMgBr and LiAlH4 to generate respectively (2R,3R)-3-hydroxy-2-methyl-3-phenylpropionic acid in homochiral form, and with 96% e.e. (S)-2-methyl-3-phenylpropionic acid and derived methyl and benzyl esters and with >94% e.e. (S)-2-methyl-3-phenylpropanol. © 1994.

Original publication

DOI

10.1016/0040-4039(94)85223-5

Type

Journal article

Journal

Tetrahedron Letters

Publication Date

11/04/1994

Volume

35

Pages

2373 - 2376