Tetrahedron letters

Asymmetric aldol and alkylation reactions mediated by the “quat” chiral auxiliary (R)-(−)-5-methyl-3, 3-dimethyl-2-pyrrolidinone

SG Davies, GJM Doisneau, JC Prodger, HJ Sanganee

文献索引：Davies; Doisneau; Prodger; Sanganee Tetrahedron Letters, 1994 , vol. 35, # 15 p. 2373 - 2376

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被引用次数: 38

摘要

Abstract 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, PhCH 2 OLi, MeOMgBr and LiAlH 4 to generate respectively (2R, 3R)-3-hydroxy-2-methyl-3- phenylpropionic acid in homochiral form, and with 96% ee (S)-2-methyl-3-phenylpropionic ...