Literature DB >> 28544237

Rhodium-Catalyzed Enantioselective Radical Addition of CX4 Reagents to Olefins.

Bo Chen1, Cheng Fang2,3, Peng Liu2, Joseph M Ready1.   

Abstract

We describe the synthetically useful enantioselective addition of Br-CX3 (X=Cl or Br) to terminal olefins to introduce a trihalomethyl group and generate optically active secondary bromides. Computational and experimental evidence supports an asymmetric atom-transfer radical addition (ATRA) mechanism in which the stereodetermining step involves outer-sphere bromine abstraction from a [(bisphosphine)RhII BrCl] complex by a benzylic radical intermediate. This mechanism appears unprecedented in asymmetric catalysis.
© 2017 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  alkenes; asymmetric catalysis; enantioselectivity; radical reactions; rhodium

Mesh：

Substances：

Year:  2017        PMID： 28544237      PMCID： PMC5672916          DOI： 10.1002/anie.201704074

Source DB:  PubMed          Journal:  Angew Chem Int Ed Engl        ISSN： 1433-7851            Impact factor:   15.336


  30 in total

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