e.g. Filippa Pettersson or Cancer Res. 75(6) , 1102-12, (2015) or 10.1002/anie.201600521

Synthesis and utility of the 3, 3-dimethyl-5-substituted-2-pyrrolidinone 'Quat'chiral auxiliary

SG Davies, DJ Dixon, GJM Doisneau, JC Prodger…

Index: Davies, Stephen G.; Dixon, Darren J.; Doisneau, Gilles J.-M.; Prodger, Jeremy C.; Sanganee, Hitesh J. Tetrahedron Asymmetry, 2002 , vol. 13, # 6 p. 647 - 658

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Citation Number: 26

Abstract

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.

N/A Structure

~89%

(5R)-3,3,5-trimethylpyrrolidin-2-one Structure

(5R)-3,3,5-trim...

(5R)-(+)-1-(2',2'-dimethyl-1'-oxopropyl)-3,3,5-trimethylpyrrolidin-2-one Structure

(5R)-(+)-1-(2',...

~93%

(5R)-3,3,5-trimethylpyrrolidin-2-one Structure

(5R)-3,3,5-trim...

L-Pyroglutamicacid Structure

L-Pyroglutamicacid

~%

(5R)-3,3,5-trimethylpyrrolidin-2-one Structure

(5R)-3,3,5-trim...

H-Pyr-OEt Structure

~%

(5R)-3,3,5-trimethylpyrrolidin-2-one Structure

(5R)-3,3,5-trim...

(5S)-5-(Hydroxymethyl)pyrrolidin-2-on Structure

(5S)-5-(Hydroxy...

~%

(5R)-3,3,5-trimethyl-1-propanoylpyrrolidin-2-one Structure

(5R)-3,3,5-trim...

L-Pyroglutamicacid Structure

L-Pyroglutamicacid

~%

(5R)-3,3,5-trimethyl-1-propanoylpyrrolidin-2-one Structure

(5R)-3,3,5-trim...

H-Pyr-OEt Structure

~%

(5R)-3,3,5-trimethyl-1-propanoylpyrrolidin-2-one Structure

(5R)-3,3,5-trim...

N/A Structure

~%

(5R)-3,3,5-trimethyl-1-propanoylpyrrolidin-2-one Structure

(5R)-3,3,5-trim...

(+)-(S)-3,3-dimethyl-5-{[(4-methylphenyl)sulfonyloxy]methyl}pyrrolidin-2-one Structure

(+)-(S)-3,3-dim...

~%

(5R)-3,3,5-trimethyl-1-propanoylpyrrolidin-2-one Structure

(5R)-3,3,5-trim...

Asymmetric aldol and alkylation reactions mediated by the “q...

[Davies; Doisneau; Prodger; Sanganee Tetrahedron Letters, 1994 , vol. 35, # 15 p. 2373 - 2376]

Asymmetric aldol and alkylation reactions mediated by the “q...

[Davies; Doisneau; Prodger; Sanganee Tetrahedron Letters, 1994 , vol. 35, # 15 p. 2373 - 2376]

Asymmetric aldol and alkylation reactions mediated by the “q...

[Davies; Doisneau; Prodger; Sanganee Tetrahedron Letters, 1994 , vol. 35, # 15 p. 2373 - 2376]

Asymmetric aldol and alkylation reactions mediated by the “q...

[Davies; Doisneau; Prodger; Sanganee Tetrahedron Letters, 1994 , vol. 35, # 15 p. 2373 - 2376]

Asymmetric aldol and alkylation reactions mediated by the “q...

[Davies; Doisneau; Prodger; Sanganee Tetrahedron Letters, 1994 , vol. 35, # 15 p. 2373 - 2376]