Readily Available [2.2.2]-Bicyclooctadienes as New Chiral Ligands for Ir(I): Catalytic, Kinetic Resolution of Allyl Carbonates

Journal of the American Chemical Society

Volumn 126, Issue 6, 2004, Pages 1628-1629

  Fischer, Christian ^a   Defieber, Christian ^a   Suzuki, Takeyuki ^a   Carreira, Erick M ^a  

^a ETH ZURICH   (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

ALKADIENE; ALLYL COMPOUND; CARBONIC ACID DERIVATIVE; CARVONE; CYCLOALKENE; IRIDIUM; IRIDIUM COMPLEX; LIGAND; UNCLASSIFIED DRUG; [2.2.2]BICYCLOOCTADIENE;

ALLYLATION; ARTICLE; ASYMMETRIC CATALYSIS; ASYMMETRIC SYNTHESIS; CHEMICAL REACTION KINETICS; CHIRALITY; COMPLEX FORMATION; ENANTIOSELECTIVITY; LIGAND BINDING; REACTION ANALYSIS;

EID: 1242276444     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja0390707     Document Type: Article

References (41)

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34. The versatility of the ligand synthesis can be exemplified by a route to another [2.2.2]-bicyclooctadiene skeleton, under current investigation. Diagram presented.
35. The fact that the phenyl ethers vary in enantioselectivity much more than the isolated carbonates, for a given conversion, is an interesting mechanistic aspect which is currently being investigated.
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37. The yields (%) and ees (%) of the phenyl ethers are: entry 1: 40, 66 ee; entry 2: 48, 80 ee; entry 3: 50, 73 ee; entry 4: 50, 77 ee; entry 5: 50, 87 ee; entry 6: 48, 87 ee; entry 7: 48, 53 ee; entry 8: 50, 80 ee; entry 9: 46, 82 ee; entry 10: 49, 86 ee; entry 11: 45, 92 ee; entry 12: 50, 45 ee; entry 13: 50, 75 ee, entry 14: 38, 72 ee; entry 15: 45, 61 ee; for details, see Supporting Information.
38. The selectivity factors were roughly calculated to be in general range between 5 and 15 for most substrates (with single entries as high as 30).
39. For a stereochemical model see Supporting Information.
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