C₂-Symmetric Bicyclo[2.2.2]octadienes as Chiral Ligands:  Their High Performance in Rhodium-Catalyzed Asymmetric Arylation of N-Tosylarylimines

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Abstract

Asymmetric synthesis of diarylmethylamines with high enantioselectivity (95−99% ee) was realized by use of a new C₂-symmetric diene ligand, (1R,4R)-2,5-diphenylbicyclo[2.2.2]octa-2,5-diene (Ph-bod*), for the rhodium-catalyzed asymmetric arylation of N-tosylarylimines with arylboroxines.

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This article has been cited by 68 ACS Journal articles (5 most recent appear below).

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  Copper-Catalyzed Petasis-Type Reaction: A General Route to α-Substituted Amides From Imines, Acid Chlorides, and Organoboron Reagents

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  The Journal of Organic Chemistry2012 Article ASAP

  • Copper-Catalyzed Petasis-Type Reaction: A General Route to α-Substituted Amides From Imines, Acid Chlorides, and Organoboron Reagents

    Marie S. T. Morin, Yingdong Lu, Daniel A. Black, and Bruce A. Arndtsen
    The Journal of Organic Chemistry2012 Article ASAP

    A copper-catalyzed Petasis-type reaction of imines, acid chlorides, and organoboranes to form α-substituted amides is described. This reaction does not require the use of activated imines or the transfer of special units from the organoboranes and ...

    Abstract | Full Text HTML | Hi-Res PDF | PDF w/ Links
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  Rhodium-Catalyzed Asymmetric Arylation of N-(tert-Butanesulfinyl)imines with Sodium Tetraarylborates

  Leleti Rajender Reddy, Aditya P. Gupta, Eric Villhauer, and Yugang Liu
  The Journal of Organic Chemistry2012 77 (2), 1095-1100

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    Leleti Rajender Reddy, Aditya P. Gupta, Eric Villhauer, and Yugang Liu
    The Journal of Organic Chemistry2012 77 (2), 1095-1100

    A diastereoselective rhodium-catalyzed arylation of N-(tert-butanesulfinyl)imines with sodium tetraarylborates is described. This method is general for constructing various chiral α-branched amines and 2-substituted pyrrolidines with high ...

    Abstract | Full Text HTML | Hi-Res PDF | PDF w/ Links
• 

  Design and Scale-Up of a Practical Enantioselective Route to 5-Phenylbicyclo[2.2.2]oct-5-en-2-one

  Stefan Abele, Roman Inauen, Jacques-Alexis Funel, and Thomas Weller
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    A practical enantioselective route to chiral 5-phenylbicyclo[2.2.2]oct-5-en-2-one 1 has been designed and developed. The target compound has been obtained as colorless crystals in 22% yield from 2-cyclohexenone, with an enantiomeric ratio higher than 99.5:...

    Abstract | Full Text HTML | Hi-Res PDF | PDF w/ Links
• 

  Rhodium-Catalyzed Asymmetric Arylation

  Ping Tian, Han-Qing Dong, and Guo-Qiang Lin
  ACS Catalysis2012 2 (1), 95-119

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    ACS Catalysis2012 2 (1), 95-119

    Rhodium-catalyzed asymmetric arylation (RCAA) reactions provide one of the most straightforward and powerful ways to introduce aryl fragments in an enantioselective manner. The discovery of novel chiral ligands and catalytic systems is a major focus in ...

    Abstract | Full Text HTML | Hi-Res PDF | PDF w/ Links
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  One-Pot Synthesis of Chiral Nonracemic Amines

  Caroline Roe, Heather Hobbs, and Robert A. Stockman
  The Journal of Organic Chemistry2011 76 (22), 9452-9459

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    Caroline Roe, Heather Hobbs, and Robert A. Stockman
    The Journal of Organic Chemistry2011 76 (22), 9452-9459

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    Abstract | Full Text HTML | Hi-Res PDF | PDF w/ Links

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