ASYMMETRIC ALDOL AND ALKYLATION REACTIONS MEDIATED BY THE QUAT CHIRALAUXILIARY (R)-(-)-5-METHYL-3,3-DIMETHYL-2-PYRROLIDINONE

Authors
DAVIES SG DOISNEAU GJM PRODGER JC SANGANEE HJ
Citation
Sg. Davies et al., ASYMMETRIC ALDOL AND ALKYLATION REACTIONS MEDIATED BY THE QUAT CHIRALAUXILIARY (R)-(-)-5-METHYL-3,3-DIMETHYL-2-PYRROLIDINONE, Tetrahedron letters, 35(15), 1994, pp. 2373-2376
Citations number
10
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
35
Issue
15
Year of publication
1994
Pages
2373 - 2376
Database
ISI
SICI code
0040-4039(1994)35:15<2373:AAAARM>2.0.ZU;2-3
Abstract
Enolates derived from the N-propionoyl derivative of the ''quat'' chir al auxiliary (R)-(-)-5-methyl-3,3-dimethyl-2-pyrrolidinon undergo high ly stereoselective aldol and alkylation reactions. Removal of the auxi liary has been demonstrated with LiOH, PhCH(2)OLi, MeOMgBr and LiA1H(4 ) to generate respectively (2R,3R)-3-hydroxy-2-methyl-3-phenylpropioni c acid in homochiral form, and with 96% e.e. (S)-2-methyl-3-phenylprop ionic acid and derived methyl and benzyl esters and with >94% e.e. (S) -2-methyl-3-phenylpropanol.