Enantioselective friedel-crafts alkylations catalyzed by bis(oxazolinyl)pyridine-scandium(III) triflate complexes

Journal of the American Chemical Society

Volumn 129, Issue 32, 2007, Pages 10029-10041

  Evans, David A ^a   Fandrick, Keith R ^a   Song, Hyun Ji ^a   Scheidt, Karl A ^a   Xu, Risheng ^a  

^a HARVARD UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CATALYST COMPLEXES; STEREOINDUCTION;

ALKYLATION; CATALYSIS; ENANTIOSELECTIVITY; METAL COMPLEXES; MOLECULAR MODELING; PYRIDINE; SCANDIUM;

ALCOHOLS;

ALDEHYDE DERIVATIVE; AMIDE; BIS(OXAZOLINYL)PYRIDINE DERIVATIVE; CARBOXYLIC ACID DERIVATIVE; ESTER DERIVATIVE; IMIDAZOLE DERIVATIVE; KETONE DERIVATIVE; PHOSPHONIC ACID DERIVATIVE; PYRIDINE DERIVATIVE; SCANDIUM; SCANDIUM TRIFLATE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; COMPLEX FORMATION; CONCENTRATION RESPONSE; CRYSTAL STRUCTURE; ENANTIOSELECTIVITY; FRIEDEL CRAFTS REACTION; LIGAND BINDING; MOLECULAR MODEL; NONLINEAR SYSTEM;

ALKYLATION; CATALYSIS; CRYSTALLOGRAPHY, X-RAY; IMIDAZOLES; INDOLES; MESYLATES; MODELS, MOLECULAR; OXAZOLES; PHOSPHONIC ACIDS; PYRIDINES; PYRROLES; SCANDIUM; STEREOISOMERISM;

EID: 34547859223     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja072976i     Document Type: Article

References (9)

1. For a review of the Friedel-Crafts reaction, see: Olah, G. A.; Krishnamurti, R.; Prakash, G. K. S. Friedel-Crafts Alkylations. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, 1991; Vol. 3, pp 293-339.
2. For examples of natural products which are relevant to the formed stereocenter, see: cycloaplysinopsin (a) Mancini, I.; Guella, G.; Zibrowius, H.; Pietra, F. Tetrahedron 2003, 59, 8757-8762.
3. 10,11-Dimethoxynareline: (b) Kam, T.; Choo, Y. J. Nat. Prod. 2004, 67, 547-552.
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9. For a review of the asymmetric Friedel-Crafts reaction, see: Bandini, M.; Melloni, A.; Umani-Ronchi, A. Angew. Chem., Int. Ed. 2004, 43, 550-556.