Ligand design for Rh(iii)-catalyzed C–H activation: an unsymmetrical cyclopentadienyl group enables a regioselective synthesis of dihydroisoquinolones† †Electronic supplementary information (ESI) available: Experimental procedures and compound characterization. CCDC 1021286. For ESI and crystallographic data in CIF or other electronic format see DOI: 10.1039/c4sc02590c Click here for additional data file. Click here for additional data file.

نویسندگان

  • Todd K. Hyster
  • Derek M. Dalton
  • Tomislav Rovis
چکیده

We report the regioselective synthesis of dihydroisoquinolones from aliphatic alkenes and O-pivaloyl benzhydroxamic acids mediated by a Rh(III) precatalyst bearing sterically bulky substituents. While the prototypical Cp* ligand provides product with low selectivity, sterically bulky Cpt affords product with excellent regioselectivity for a range of benzhydroxamic acids and alkenes. Crystallographic evidence offers insight as to the source of the increased regioselectivity.

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منابع مشابه

Heptamethylindenyl (Ind*) enables diastereoselective benzamidation of cyclopropenes via Rh(iii)-catalyzed C–H activation† †Electronic supplementary information (ESI) available: Experimental procedures and compound characterization. CCDC 1472771. For ESI and crystallographic data in CIF or other electronic format see DOI: 10.1039/c6sc02587k Click here for additional data file. Click here for additional data file. Click here for additional data file.

The diastereoselective coupling of O-substituted arylhydroxamates and cyclopropenes mediated by Rh(III) catalysis was successfully developed. Through ligand development, the diastereoselectivity of this reaction was improved using a heptamethylindenyl (Ind*) ligand, which has been rationalized using quantum chemical calculations. In addition, the nature of the O-substituted ester of benzhydroxa...

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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