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 |
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| 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 |
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| Institution: | Departamento de Química Inorgánica, Instituto de Ciencia de Materiales de Aragón, Universidad de Zaragoza-Consejo Superior de Investigaciones Científicas, 50009 Zaragoza, Spain. dcarmona@unizar.es |
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| Abstract: | The 1,3-dipolar cycloaddition reaction of C,N-diphenylnitrone with methacrolein is efficiently catalyzed by the rhodium diphosphine compound (SRh,RC)-(eta5-C5Me5)Rh(R-Prophos)(H2O)](SbF6)2 R-Prophos = (R)-(+)-1,2-bis(diphenylphosphino)-propane, 1.SbF6]; 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 (SRh,RC)-(eta5-C5Me5)Rh(R-Prophos)(methacrolein)](SbF6)2 (7.SbF6) allows us to interpret the observed selectivity. |
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