Journal
ACS CATALYSIS
Volume 6, Issue 2, Pages 1198-1204Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acscatal.5b02136
Keywords
asymmetric catalysis; chiral Bronsted acid; perfluorinated aryls; cycloaddition; imino-ene reaction
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Funding
- JSPS [21750087]
- Grants-in-Aid for Scientific Research [21750087] Funding Source: KAKEN
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Perfluorinated aryl-incorporating chiral monophosphoric acids were used for highly stereoselective reactions of N-acyl and N-acyloxy aldimines with styrenes. Their electronic and steric profiles were established in comparison with those of phenyl, binaphthyl, and partially fluorinated aryls. The [4 + 2] cycloaddition reactions of N-benzoyl aldimines with alkenes proceeded with excellent diastereo- and enantioselectivities in the presence of the perfluorophenyl-incorporating chiral mono phosphoric acid catalysts 1a and 1c. The stereoselective elaboration of polysubstituted cydoadducts to amines is described. The imino-ene reactions of N-Fmoc imines with alkenes have been successfully developed in a three-component manner. This process uses aldehydes, 9-fluorenylmethyl carbamate, and alkenes in the presence of a chiral monophosphoric acid catalyst, 2a, possessing an F(10)binaphthyl skeleton.
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