Synthesis and utility of the 3,3-dimethyl-5-substituted-2-pyrrolidinone 'Quat' chiral auxiliary
The synthesis and utility of the 3,3-dimethyl-5-substituted-2-pyrrolidinone 'Quat' chiral auxiliary in stereoselective enolate reactions of attached N-acyl side chains combined with the mild and non-racemising conditions required for the ultimate removal of the chiral side chain is described.
Davies, Stephen G.,Dixon, Darren J.,Doisneau, Gilles J.-M.,Prodger, Jeremy C.,Sanganee, Hitesh J.
p. 647 - 658
(2007/10/03)
Asymmetric aldol and alkylation reactions mediated by the 'quat' chiral auxiliary (R)-(-)-5-methyl-3,3-dimethyl-2-pyrrolidinone
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.
Davies,Doisneau,Prodger,Sanganee
p. 2373 - 2376
(2007/10/02)
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