2,3-Dihydroimidazo[1,2-a]pyridines: A new class of enantioselective acyl transfer catalysts and their use in kinetic resolution of alcohols

Journal of the American Chemical Society

Volumn 126, Issue 39, 2004, Pages 12226-12227

  Birman, Vladimir B ^a   Uffman, Eric W ^a   Jiang, Hui ^a   Li, Ximin ^a   Kilbane, Corey J ^a  

^a WASHINGTON UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

2 HALOPYRIDINE; 2 PHENYL 2,3 DIHYDROIMIDAZO[1,2 A]PYRIDINE; 2,3 DIHYDROIMIDAZO[1,2 A]PYRIDINE; ALCOHOL DERIVATIVE; CARBONYL DERIVATIVE; ENZYME; METHANOL; PHENYLETHYLCARBINOL; PHENYLGLYCINOL; PYRIDINE DERIVATIVE; UNCLASSIFIED DRUG;

ACETYLATION; ACYLATION; ARTICLE; BROMINATION; CATALYST; CHEMICAL INTERACTION; CHEMICAL STRUCTURE; CHIRALITY; CONFORMATION; CYCLIZATION; ENANTIOSELECTIVITY; ESTERIFICATION; KINETICS; NUCLEAR MAGNETIC RESONANCE; RACEMIC MIXTURE; STEREOCHEMISTRY;

EID: 4644304800     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja0491477     Document Type: Article

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39. Preparative-scale resolution of 1-naphthyl methyl carbinol (2.416 g, 14.0 mmol) gave the ester in 52% yield and 82.5% ee and the unreacted alcohol in 45% yield and 98.8% ee, which corresponds to 54% conversion and 52:1 selectivity. 68% of the catalyst was recovered. See Supporting Information for more details.