Practical asymmetric synthesis of a potent PDE4 inhibitor via stereoselective enolate alkylation of a chiral aryl-heteroaryl secondary tosylate

Journal of Organic Chemistry

Volumn 70, Issue 8, 2005, Pages 3021-3030

  O'Shea, Paul D ^a   Chen, Cheng Yi ^b   Chen, Weirong ^b   Dagneau, Philippe ^a   Frey, Lisa F ^b   Grabowski, Edward J J ^b   Marcantonio, Karen M ^b   Reamer, Robert A ^b   Tan, Lushi ^b   Tillyer, Richard D ^b   Roy, Amélie ^a   Wang, Xin ^a   Zhao, Dalian ^b  

^a MERCK FROSST CENTRE FOR THERAPEUTIC RESEARCH   (Canada)

^b MERCK RESEARCH LABORATORIES   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ACTIVATION ANALYSIS; CARBOXYLATION; CATALYSIS; CHROMATOGRAPHIC ANALYSIS; ESTERS; HYDROGENATION; METHANE; REACTION KINETICS; STEREOCHEMISTRY; SUBSTITUTION REACTIONS; SYNTHESIS (CHEMICAL);

DISPLACEMENT REACTIONS; ENANTIOSELECTIVITY; OPTICAL PURITY;

CATALYSTS;

2 {5 [1 [3 (CYCLOPROPYLOXY) 4 (DIFLUOROMETHOXY) PHENYL] 2 (1 OXIDOPYRIDIN 3 YL)ETHYL] 1,3 THIAZOL 2 YL} 1,1,1,3,3,3 HEXAFLUROPROPAN 2 OL; ALDEHYDE; ETHYL 3 PYRIDYLACETATE N OXIDE; KETONE; L 869298; LITHIUM; PHOSPHODIESTERASE IV INHIBITOR; THIAZOLE; TOLUENESULFONIC ACID DERIVATIVE; UNCLASSIFIED DRUG;

ALKYLATION; ARTICLE; ASYMMETRIC CATALYSIS; ASYMMETRIC SYNTHESIS; CHIRALITY; DECARBOXYLATION; DEPROTECTION REACTION; DRUG STRUCTURE; DRUG SYNTHESIS; ENANTIOSELECTIVITY; PROTON NUCLEAR MAGNETIC RESONANCE; RING OPENING; SAPONIFICATION; STEREOCHEMISTRY;

3',5'-CYCLIC-NUCLEOTIDE PHOSPHODIESTERASE; COMBINATORIAL CHEMISTRY TECHNIQUES; CYCLIC N-OXIDES; ENZYME INHIBITORS; MAGNETIC RESONANCE SPECTROSCOPY; MOLECULAR STRUCTURE; PYRIDINES; STEREOISOMERISM;

EID: 20244386861     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo048156v     Document Type: Article

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