Bicyclo[3.2.0]heptane-based enamides by Ru/PNNP-catalyzed enantioselective ficini reactions: Scope and application in ligand design

Synthesis

Volumn 44, Issue 4, 2012, Pages 513-526

  Schotes, Christoph ^a   Bigler, Raphael ^a   Mezzetti, Antonio ^a  

^a ETH ZURICH   (Switzerland)

Author keywords

asymmetric catalysis; biaryls; bicyclic compounds; cycloaddition; ligands; phosphorus; ruthenium

Indexed keywords

ALKYLIDENES; ASYMMETRIC CATALYSIS; BENZYLIDENE; BIARYLS; BICYCLIC COMPOUNDS; BIDENTATE LIGANDS; CHLORIDE ABSTRACTION; DIPHOSPHITE; ENAMIDES; ENANTIOSELECTIVE; HIGH YIELD; KETO ESTER; LIGAND DESIGN; SELECTED EXAMPLES; STRUCTURAL FEATURE;

CATALYSIS; CHLORINE COMPOUNDS; CYCLOADDITION; HEPTANE; IRIDIUM; OLEFINS; PALLADIUM COMPOUNDS; PHOSPHORUS; RHODIUM; RUTHENIUM; RUTHENIUM COMPOUNDS;

LIGANDS;

DIBENZYL 2 (1,3 DIPHENYLALLYL)MALONATE; DIMETHYL 2 (1,3 DIPHENYLALLYL)MALONATE; DIMETHYL 2 METHYLSUCCINATE; HEPTANE DERIVATIVE; METHYL 2 (ACETYLAMINO)PROPANOATE; N (CYCLOHEXYLETHYNYL) N METHYLMETHANESULFONAMIDE; N BENZYL N [7 CYCLOHEXYL 4 [(2,4,8,10 TETRA TERT BUTYLDIBENZO[D,F][1,3,2] DIOXAPHOSPHEPIN 6 YL)OXY] 5 [[(2,4,8,10 TETRA TERT BUTYLDIBENZO[D,F][1,3,2]DIOXAPHOSPHEPIN 6 YL)OXY]METHYL]BICYCLO[3.2.0]HEPT 6 EN 6 YL] 4 METHYLBENZENESULFONAMIDE; N BENZYL N [7 CYCLOHEXYL 4 [(DIBENZO[D,F][1,3,2]DIOXAPHOSPHEPIN 6 YL)OXY] 5 [[(DIBENZO[D,F][1,3,2]DIOXAPHOSPHEPIN 6 YL)OXY]METHYL]BICYCLO[3.2.0]HEPT 6 EN 6 YL] 4 METHYLBENZENESULFONAMIDE; N BENZYL N [7 CYCLOHEXYL 4 HYDROXY 5 (HYDROXYMETHYL)BICYCLO[3.2.0]HEPT 6 EN 6 YL] 4 METHYLBENZENESULFONAMIDE; TERT BUTYL 2 [(TERT BUTYLDIMETHYLSILYL)OXY] 7 (PHENYLTHIO)BICYCLO[3.2.0]HEPTA 2,6 DIENE 1 CARBOXYLATE; TERT BUTYL 2 OXO 7 (PHENYLTHIO)BICYCLO[3.2.0]HEPT 6 ENE 1 CARBOXYLATE; TERT BUTYL 6 CYCLOHEXYL 2 [(DIBENZO[D,F][1,3,2]DIOXAPHOSPHEPIN 6 YL)OXY] 7 (N METHYLMETHYLSULFONAMIDO)BICYCLO[3.2.0]HEPT 6 ENE 1 CARBOXYLATE; TERT BUTYL 6 CYCLOHEXYL 7 (N METHYLMETHYLSULFONAMIDO) 2 OXOBICYCLO[3.2.0]HEPT 6 ENE 1 CARBOXYLATE; TERT BUTYL 7 (N BENZYL 4 METHYLPHENYLSULFONAMIDO) 2 [(TERT BUTYLIMETHYSILYL)OXY] 6 CYCLOHEXYLBICYCLO[3.2.0]HEPTA 2,6 DIENE 1 CARBOXYLATE; TERT BUTYL 7 (N BENZYL 4 METHYLPHENYLSULFONAMIDO) 6 CYCLOHEXYL 2 [(1,3,2 DIOXAPHOSPHOLAN 2 YL)OXY]BICYCLO[3.2.0]HEPT 6 ENE 1 CARBOXYLATE; TERT BUTYL 7 (N BENZYL 4 METHYLPHENYLSULFONAMIDO) 6 CYCLOHEXYL 2 [(DIBENZO[D,F][1,3,2]DIOXAPHOSPHEPIN 6 YL)OXY]BICYCLO[3.2.0]HEPT 6 ENE 1 CARBOXYLATE; TERT BUTYL 7 (N BENZYL 4 METHYLPHENYLSULFONAMIDO) 6 CYCLOHEXYL 2 HYDROXY 2 METHYLBICYCLO[3.2.0]HEPTA 3,6 DIENE 1 CARBOXYLATE; TERT BUTYL 7 (N BENZYL 4 METHYLPHENYLSULFONAMIDO) 6 CYCLOHEXYL 2 HYDROXYBICYCLO[3.2.0]HEPT 6 ENE 1 CARBOXYLATE; TERT BUTYL 7 (N BENZYL 4 METHYLPHENYLSULFONAMIDO) 6 CYCLOHEXYL 2 OXOBICYCLO[3.2.0]HEPTA 3,6 DIENE 1 CARBOXYLATE; TERT BUTYL 7 (N BENZYL4 METHYLPHENYLSULFONAMIDO) 6 CYCLOHEXYL 2 [(DINAPHTHO[2,1 D:1',2' F][1,3,2]DIOXAPHOSPHEPIN 4 YL)OXY]BICYCLO[3.2.0]HEPT 6 ENE 1 CARBOXYLATE; UNCLASSIFIED DRUG;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CATALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; CHROMATOGRAPHY; COLUMN CHROMATOGRAPHY; CRYSTALLIZATION; CYCLOADDITION; DEGRADATION; ELECTROPHILICITY; ENANTIOSELECTIVITY; ESTERIFICATION; FICINI REACTION; FLUORINATION; HYDROGENATION; HYDROXYLATION; MICHAEL ADDITION; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; NUCLEOPHILICITY; OXIDATION; PHOSPHORUS NUCLEAR MAGNETIC RESONANCE; POLARIZATION; REACTION TIME;

EID: 84857032454     PISSN: 00397881     EISSN: 1437210X     Source Type: Journal    
DOI: 10.1055/s-0031-1289679     Document Type: Article

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