The Complete Characterization of a Rhodium Lewis Acid−Dipolarophile Complex as an Intermediate for the Enantioselective Catalytic 1,3-Dipolar Cycloaddition of C,N-Diphenylnitrone to Methacrolein

The 1,3-dipolar cycloaddition reaction of C,N-diphenylnitrone with methacrolein is efficiently catalyzed by the rhodium diphosphine compound (S Rh,R C)-[(η5-C5Me5)Rh(R-Prophos)(H2O)](SbF6)2 [R-Prophos = (R)-(+)-1,2-bis(diphenylphosphino)-propane, 1·SbF 6 ]; the asymmetric catalytic process occurs wi...

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Bibliographic Details
Published in:Journal of the American Chemical Society 2004-03, Vol.126 (9), p.2716-2717
Main Authors: Carmona, Daniel, Lamata, M. Pilar, Viguri, Fernando, Rodríguez, Ricardo, Oro, Luis A, Balana, Ana I, Lahoz, Fernando J, Tejero, Tomás, Merino, Pedro, Franco, Santiago, Montesa, Isabel
Format: Article
Language:English
Subjects:
Acrolein - chemistry
Alkenes - chemistry
Catalysis
Cyclization
Isoxazoles - chemical synthesis
Nitrogen Oxides - chemistry
Organometallic Compounds - chemistry
Rhodium - chemistry
Stereoisomerism
X-Ray Diffraction
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Summary:The 1,3-dipolar cycloaddition reaction of C,N-diphenylnitrone with methacrolein is efficiently catalyzed by the rhodium diphosphine compound (S Rh,R C)-[(η5-C5Me5)Rh(R-Prophos)(H2O)](SbF6)2 [R-Prophos = (R)-(+)-1,2-bis(diphenylphosphino)-propane, 1·SbF 6 ]; the asymmetric catalytic process occurs with reversal of regioselectivity, perfect endo selectivity, and up to 92% ee. The complete (NMR and X-ray analysis) characterization of the involved intermediate (S Rh,R C)-[(η5-C5Me5)Rh(R-Prophos)(methacrolein)](SbF6)2 (7·SbF 6 ) allows us to interpret the observed selectivity.
ISSN:0002-7863
1520-5126
DOI:10.1021/ja031995z