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

Stephen G. Davies; Darren J. Dixon; Gilles J M Doisneau; Jeremy C. Prodger; Hitesh J. Sanganee

doi:10.1016/S0957-4166(02)00166-0

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

Stephen G. Davies
, Darren J. Dixon
, Gilles J M Doisneau
, Jeremy C. Prodger
, Hitesh J. Sanganee

Research output: Contribution to journal › Article › peer-review

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. © 2002 Elsevier Science Ltd. All rights reserved.

Original language	English
Pages (from-to)	647-658
Number of pages	11
Journal	Tetrahedron Asymmetry
Volume	13
Issue number	6
DOIs	https://doi.org/10.1016/S0957-4166(02)00166-0
Publication status	Published - 19 Apr 2002

Keywords

Asymmetric synthesis and induction; Chiral auxiliary (stereoselective prepn. and use of chiral dimethylpyrrolidinone auxiliaries); Alkylation (stereoselective; stereoselective prepn. of N-[phenyl(methyl)propanoyl]pyrrolidinones via asym. alkylation of chiral N-acyldimethyl(alkyl)pyrrolidinones with alkyl halides); Aldol condensation (stereoselective; stereoselective prepn. of phenyl(hydroxy)methylpropanoic acid via asym. aldol condensation of N-propanoyl(trimethyl)pyrrolidinone with benzaldehyde followed by cleavage from the chiral auxiliary)

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

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. {\textcopyright} 2002 Elsevier Science Ltd. All rights reserved.",

keywords = "Asymmetric synthesis and induction; Chiral auxiliary (stereoselective prepn. and use of chiral dimethylpyrrolidinone auxiliaries); Alkylation (stereoselective; stereoselective prepn. of N-[phenyl(methyl)propanoyl]pyrrolidinones via asym. alkylation of chiral N-acyldimethyl(alkyl)pyrrolidinones with alkyl halides); Aldol condensation (stereoselective; stereoselective prepn. of phenyl(hydroxy)methylpropanoic acid via asym. aldol condensation of N-propanoyl(trimethyl)pyrrolidinone with benzaldehyde followed by cleavage from the chiral auxiliary)",

author = "Davies, \{Stephen G.\} and Dixon, \{Darren J.\} and Doisneau, \{Gilles J M\} and Prodger, \{Jeremy C.\} and Sanganee, \{Hitesh J.\}",

year = "2002",

month = apr,

day = "19",

doi = "10.1016/S0957-4166(02)00166-0",

language = "English",

volume = "13",

pages = "647--658",

journal = "Tetrahedron Asymmetry",

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TY - JOUR

T1 - Synthesis and utility of the 3,3-dimethyl-5-substituted-2-pyrrolidinone 'Quat' chiral auxiliary

AU - Davies, Stephen G.

AU - Dixon, Darren J.

AU - Doisneau, Gilles J M

AU - Prodger, Jeremy C.

AU - Sanganee, Hitesh J.

PY - 2002/4/19

Y1 - 2002/4/19

N2 - 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. © 2002 Elsevier Science Ltd. All rights reserved.

AB - 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. © 2002 Elsevier Science Ltd. All rights reserved.

KW - Asymmetric synthesis and induction; Chiral auxiliary (stereoselective prepn. and use of chiral dimethylpyrrolidinone auxiliaries); Alkylation (stereoselective; stereoselective prepn. of N-[phenyl(methyl)propanoyl]pyrrolidinones via asym. alkylation of chi

U2 - 10.1016/S0957-4166(02)00166-0

DO - 10.1016/S0957-4166(02)00166-0

M3 - Article

SN - 0957-4166

VL - 13

SP - 647

EP - 658

JO - Tetrahedron Asymmetry

JF - Tetrahedron Asymmetry

IS - 6

ER -

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

Abstract

Keywords

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