Development and investigation of a site selective palladium-catalyzed 1,4-difunctionalization of isoprene using pyridine–oxazoline ligands† †Electronic supplementary information (ESI) available: Detailed experimental procedures, reaction optimization data, and spectroscopic data of all new compounds. See DOI: 10.1039/c4sc03074e Click here for additional data file.

نویسندگان

  • Matthew S. McCammant
  • Matthew S. Sigman
چکیده

Palladium-catalyzed 1,4-difunctionalizations of isoprene that produce skipped polyenes are reported. Complex isomeric product mixtures are possible as a result of the difficult-to-control migratory insertion of isoprene into a Pd-alkenyl bond, but good site selectivity has been achieved using easily accessible Pyrox ligands. Mechanistic studies suggest that the control of insertion is the result of the unique electronic asymmetry and steric properties of the ligand.

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Enantioselective palladium(0)-catalyzed intramolecular cyclopropane functionalization: access to dihydroquinolones, dihydroisoquinolones and the BMS-791325 ring system† †Electronic supplementary information (ESI) available: Experimental procedures and characterization of all new compounds. CCDC 1401582. For ESI and crystallographic data in CIF or other electronic format see DOI: 10.1039/c5sc01909e Click here for additional data file. Click here for additional data file.

Taddol-based phosphoramidite ligands enable enantioselective palladium(0)-catalyzed C–H arylation of cyclopropanes. The cyclized products are obtained in high yields and enantioselectivities. The reported method provides efficient access to a broad range of synthetically attractive cyclopropyl containing dihydroquinolones and dihydroisoquinolones as well as allows for an efficient enantioselect...

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عنوان ژورنال:

دوره 6  شماره 

صفحات  -

تاریخ انتشار 2015