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
- 11 February 2004
- journal article
- research article
- Published by American Chemical Society (ACS) in Journal of the American Chemical Society
- Vol. 126 (9) , 2716-2717
- https://doi.org/10.1021/ja031995z
Abstract
The 1,3-dipolar cycloaddition reaction of C,N-diphenylnitrone with methacrolein is efficiently catalyzed by the rhodium diphosphine compound (SRh,RC)-[(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 (SRh,RC)-[(η5-C5Me5)Rh(R-Prophos)(methacrolein)](SbF6)2 (7·SbF 6) allows us to interpret the observed selectivity.Keywords
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