Stereoselective synthesis of chiral 4-(1-Chloroalkyl)-β-lactams starting from amino acids and their transformation into functionalized chiral azetidines and pyrrolidines

Journal of Organic Chemistry

Volumn 75, Issue 17, 2010, Pages 5934-5940

  Dekeukeleire, Stijn ^a   Dhooghe, Matthias ^a   Törnroos, Karl W ^b   De Kimpe, Norbert ^a  

^a GHENT UNIVERSITY   (Belgium)

^b UNIVERSITY OF BERGEN   (Norway)

Author keywords

[No Author keywords available]

Indexed keywords

AZETIDINES; CHIRAL BUILDING BLOCKS; DIASTEREOMERIC RATIOS; FUNCTIONALIZED; ORGANOCATALYTIC; PYRROLIDINES; STARTING MATERIALS; STEREO-SELECTIVE; STEREOSELECTIVE SYNTHESIS; THREE-STEP APPROACH;

ALDEHYDES; AMIDES; AMINO ACIDS; BUILDING MATERIALS; ORGANIC ACIDS;

STEREOSELECTIVITY;

1 ALLYL 2 (1 CHLORO 3 METHYLBUTYL) 3 METHOXYAZETIDINE; 1 ALLYL 3 CHLORO 4 METHOXY 2 (2 METHYLPROPYL) PYRROLIDINE; 1 ALLYL 4 (1 CHLORO 3 METHYLBUTYL) 3 METHOXYAZETIDIN 2 ONE; 1 BENZYL 2 (1 CHLORO 2 METHYLBUTYL) 3 METHOXYAZETIDINE; 1 BENZYL 3 CHLORO 2 (1 METHYLPROPYL) 4 METHOXYPYRROLIDINE; 1 BENZYL 4 (1 CHLORO 2 METHYLBUTYL) 3 METHOXYAZETIDIN 2 ONE; 1 BUTYL 3 CHLORO 4 HYDROXY 2 (2 METHYLPROPYL) PYRROLIDINE; 2 (1 CHLORO 2 METHYLBUTYL) 3 PHENOXY 1 PROPYLAZETIDINE; 2 (1 CHLORO 2 PHENYLETHYL) 1 ISOPROPYL 3 PHENOXYAZETIDINE; 2 BENZYL 3 CHLORO 1 ISOPROPYL 4 PHENOXYPYRROLIDINE; 2 BENZYL 4 BENZYLOXY 3 CHLORO 1 CYCLOHEXYLPYRROLIDINE; 3 BENZYLOXY 1 BUTYL 2 (1 CHLORO 3 METHYLBUTYL) AZETIDINE; 3 BENZYLOXY 1 BUTYL 4 (1 CHLORO 3 METHYLBUTYL) AZETIDIN 2 ONE; 3 BENZYLOXY 2 (1 CHLORO 2 METHYLPROPYL) 1 ISOPROPYLAZETIDINE; 3 BENZYLOXY 2 (1 CHLORO 2 PHENYLETHYL) 1 CYCLOHEXYLAZETIDINE; 3 BENZYLOXY 4 (1 CHLORO 2 METHYLPROPYL) 1 ISOPROPYLAZETIDIN 2 ONE; 3 BENZYLOXY 4 (1 CHLORO 2 PHENYLETHYL) 1 CYCLOHEXYLAZETIDIN 2 ONE; 3 CHLORO 2 (1 METHYLPROPYL) 4 PHENOXY 1 PROPYLPYRROLIDINE; 4 (1 CHLORO 2 METHYLBUTYL) 3 PHENOXY 1 PROPYLAZETIDIN 2 ONE; 4 (1 CHLORO 2 PHENYLETHYL) 1 ISOPROPYL 3 PHENOXYAZETIDIN 2 ONE; 4 BENZYLOXY 1 BUTYL 3 CHLORO 2 (2 METHYLPROPYL) PYRROLIDINE; 4 BENZYLOXY 3 CHLORO 1,2 DIISOPROPYLPYRROLIDINE; ALDEHYDE DERIVATIVE; AMINO ACID; AZETIDINE DERIVATIVE; BETA LACTAM DERIVATIVE; PYRROLIDINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; BIOTRANSFORMATION; CHIRALITY; CHLORINATION; DIASTEREOISOMER; DRUG SYNTHESIS; DRUG TRANSFORMATION; ENANTIOMER; STAUDINGER REACTION; STEREOCHEMISTRY;

AMINO ACIDS; AZETIDINES; BETA-LACTAMS; MOLECULAR CONFORMATION; PYRROLIDINES; STEREOISOMERISM;

EID: 77956164335     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo101220q     Document Type: Article

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