Unknown

Dataset Information

0

Heptamethylindenyl (Ind*) enables diastereoselective benzamidation of cyclopropenes via Rh(iii)-catalyzed C-H activation.

ABSTRACT: 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 benzhydroxamic acid proved important for high diastereoselectivity. This transformation tolerates a variety of benzamides and cyclopropenes that furnish cyclopropa[c]dihydroisoquinolones with high diastereocontrol, which could then be easily transformed into synthetically useful building blocks for pharmaceuticals and bio-active molecules.

SUBMITTER: Semakul N 

PROVIDER: S-EPMC5354047 | biostudies-literature | 2017 Feb

REPOSITORIES: biostudies-literature

Json Xml
altmetric image

Publications

Heptamethylindenyl (Ind*) enables diastereoselective benzamidation of cyclopropenes <i>via</i> Rh(iii)-catalyzed C-H activation.

Semakul Natthawat N   Jackson Kelvin E KE   Paton Robert S RS   Rovis Tomislav T  

Chemical science 20160923 2

The diastereoselective coupling of <i>O</i>-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 <i>O</i>-substituted ester of benzhydroxamic acid proved important for high diastereoselectivity. This transformation tolerates a  ...[more]

Similar Datasets

Unknown Rh(III)-catalyzed cyclopropanation initiated by C-H activation: ligand development enables a diastereoselective [2 + 1] annulation of N-enoxyphthalimides and alkenes.
| S-EPMC4140504 | biostudies-literature
Unknown Cobalt-Catalyzed Diastereoselective and Enantioselective Hydrosilylation of Achiral Cyclopropenes.
| S-EPMC7467819 | biostudies-literature
Unknown Rh(III)-catalyzed oxidative coupling of unactivated alkenes via C-H activation.
| S-EPMC3031716 | biostudies-literature
Unknown Rh(III)-Catalyzed Diastereoselective C-H Bond Addition/Cyclization Cascade of Enone Tethered Aldehydes.
| S-EPMC4762265 | biostudies-literature
Unknown Ligand Design for Rh(III)-Catalyzed C-H Activation: An Unsymmetrical Cyclopentadienyl Enables a Regioselective Synthesis of Dihydroisoquinolones.
| S-EPMC4256080 | biostudies-literature
Unknown Direct Regio- and Diastereoselective Synthesis of ?-Lactams from Acrylamides and Unactivated Alkenes Initiated by Rh<sup>III</sup> -Catalyzed C-H Activation.
| S-EPMC7097884 | biostudies-literature
Unknown Rhodium(III)-Catalyzed C-H Activation Mediated Synthesis of Isoquinolones from Amides and Cyclopropenes.
| S-EPMC4206942 | biostudies-literature
Unknown Copper-Catalyzed Enantio- and Diastereoselective Addition of Silicon Nucleophiles to 3,3-Disubstituted Cyclopropenes.
| S-EPMC6899982 | biostudies-literature
Unknown Rh(iii)-catalyzed C-7 arylation of indolines with arylsilanes <i>via</i> C-H activation.
| S-EPMC9064675 | biostudies-literature
Unknown Rh(III)-Catalyzed C-H Activation-Initiated Directed Cyclopropanation of Allylic Alcohols.
| S-EPMC6980370 | biostudies-literature