Bruce A Arndtsen

Summary

Affiliation: McGill University
Country: Canada

Publications

  1. doi request reprint Metal-catalyzed one-step synthesis: towards direct alternatives to multistep heterocycle and amino acid derivative formation
    Bruce A Arndtsen
    Department of Chemistry, McGill University, 801 Sherbrooke St W Montreal, QC H3A 2K6, Canada
    Chemistry 15:302-13. 2009
  2. doi request reprint Palladium-catalyzed multicomponent synthesis of 2-imidazolines from imines and acid chlorides
    Boran Xu
    Department of Chemistry, McGill University, 801 Sherbrooke Street West, Montreal, QC H3A 2K6, Canada
    Molecules 17:13759-68. 2012
  3. doi request reprint Copper-catalyzed Petasis-type reaction: a general route to α-substituted amides from imines, acid chlorides, and organoboron reagents
    Marie S T Morin
    Department of Chemistry, McGill University, 801 Sherbrooke St West, Montreal, Quebec H3A 2K6, Canada
    J Org Chem 77:2013-7. 2012
  4. doi request reprint Hydrogen-bonding asymmetric metal catalysis with alpha-amino acids: a simple and tunable approach to high enantioinduction
    Yingdong Lu
    Department of Chemistry, McGill University, 801 Sherbrooke Street West, Montreal, QC H3A 2K6, Canada
    J Am Chem Soc 131:11284-5. 2009
  5. doi request reprint Palladium-catalyzed carbonylative cross-coupling with imines: a multicomponent synthesis of imidazolones
    Ali R Siamaki
    Department of Chemistry, McGill University, 801 Sherbrooke Street West, Montreal, Quebec, H3A 2K6, Canada
    J Org Chem 73:1135-8. 2008
  6. doi request reprint A palladium-catalyzed multicomponent synthesis of imidazolinium salts and imidazolines from imines, acid chlorides, and carbon monoxide
    Kraig Worrall
    Department of Chemistry, McGill University, 801 Sherbrooke Street West, Montreal, Quebec, Canada H3A 2K6
    J Org Chem 76:170-80. 2011
  7. ncbi request reprint Direct synthesis of pyrroles from imines, alkynes, and acid chlorides: an isocyanide-mediated reaction
    Daniel J St Cyr
    Department of Chemistry, McGill University, 801 Sherbrooke Street West, Montreal, Quebec H3A 2K6, Canada
    Org Lett 9:449-52. 2007
  8. ncbi request reprint Direct, palladium-catalyzed, multicomponent synthesis of beta-lactams from imines, acid chloride, and carbon monoxide
    Rajiv Dhawan
    Department of Chemistry, McGill University, 801 Sherbrooke Street West, Montreal, Quebec H3A 2K6, Canada
    Org Lett 8:3927-30. 2006
  9. doi request reprint A direct phosphine-mediated synthesis of pyrroles from acid chlorides and alpha,beta-unsaturated imines
    Yingdong Lu
    Department of Chemistry, McGill University, 801 Sherbrooke Street W, Montreal QC H3A 2K6, Canada
    Org Lett 11:1369-72. 2009
  10. ncbi request reprint A direct, one step synthesis of imidazoles from imines and acid chlorides: a palladium catalyzed multicomponent coupling approach
    Ali R Siamaki
    Department of Chemistry, McGill University, 801 Sherbrooke Street West, Montreal, Quebec H3A 2K6, Canada
    J Am Chem Soc 128:6050-1. 2006

Collaborators

  • Boran Xu
  • Yingdong Lu
  • Marie S T Morin
  • Rajiv Dhawan
  • Daniel A Black
  • Ali R Siamaki
  • Daniel J St Cyr
  • Kraig Worrall
  • Rania D Dghaym
  • Sara Aly
  • Sébastien Bontemps
  • Daniel J St-Cyr
  • Tim C Johnstone
  • Nicolas Martin

Detail Information

Publications16

  1. doi request reprint Metal-catalyzed one-step synthesis: towards direct alternatives to multistep heterocycle and amino acid derivative formation
    Bruce A Arndtsen
    Department of Chemistry, McGill University, 801 Sherbrooke St W Montreal, QC H3A 2K6, Canada
    Chemistry 15:302-13. 2009
    ..Overall, this allows the synthesis of each these products in one step, in high yield, with minimal waste, and with straightforward access to product diversity...
  2. doi request reprint Palladium-catalyzed multicomponent synthesis of 2-imidazolines from imines and acid chlorides
    Boran Xu
    Department of Chemistry, McGill University, 801 Sherbrooke Street West, Montreal, QC H3A 2K6, Canada
    Molecules 17:13759-68. 2012
    ..Combining this reaction with subsequent nitrogen deprotection provides an overall synthesis of imidazolines from multiple available building blocks...
  3. doi request reprint Copper-catalyzed Petasis-type reaction: a general route to α-substituted amides from imines, acid chlorides, and organoboron reagents
    Marie S T Morin
    Department of Chemistry, McGill University, 801 Sherbrooke St West, Montreal, Quebec H3A 2K6, Canada
    J Org Chem 77:2013-7. 2012
    ..This reaction does not require the use of activated imines or the transfer of special units from the organoboranes and represent a useful generalization of the Petasis reaction...
  4. doi request reprint Hydrogen-bonding asymmetric metal catalysis with alpha-amino acids: a simple and tunable approach to high enantioinduction
    Yingdong Lu
    Department of Chemistry, McGill University, 801 Sherbrooke Street West, Montreal, QC H3A 2K6, Canada
    J Am Chem Soc 131:11284-5. 2009
    ..The latter is illustrated in the copper-catalyzed alkynylation of imines in up to 99% ee...
  5. doi request reprint Palladium-catalyzed carbonylative cross-coupling with imines: a multicomponent synthesis of imidazolones
    Ali R Siamaki
    Department of Chemistry, McGill University, 801 Sherbrooke Street West, Montreal, Quebec, H3A 2K6, Canada
    J Org Chem 73:1135-8. 2008
    ..Overall, this methodology provides an alternative approach to imidazolones from five simple and readily available building blocks via a one-pot, multicomponent process...
  6. doi request reprint A palladium-catalyzed multicomponent synthesis of imidazolinium salts and imidazolines from imines, acid chlorides, and carbon monoxide
    Kraig Worrall
    Department of Chemistry, McGill University, 801 Sherbrooke Street West, Montreal, Quebec, Canada H3A 2K6
    J Org Chem 76:170-80. 2011
    ..The subsequent removal of the nitrogen substituent(s) provides an overall synthesis of imidazolines...
  7. ncbi request reprint Direct synthesis of pyrroles from imines, alkynes, and acid chlorides: an isocyanide-mediated reaction
    Daniel J St Cyr
    Department of Chemistry, McGill University, 801 Sherbrooke Street West, Montreal, Quebec H3A 2K6, Canada
    Org Lett 9:449-52. 2007
    ..Mechanistic studies suggest this process proceeds via the generation of imino analogues of munchnones, which can undergo in situ coupling with alkynes to liberate isocyanate and form the pyrrole product...
  8. ncbi request reprint Direct, palladium-catalyzed, multicomponent synthesis of beta-lactams from imines, acid chloride, and carbon monoxide
    Rajiv Dhawan
    Department of Chemistry, McGill University, 801 Sherbrooke Street West, Montreal, Quebec H3A 2K6, Canada
    Org Lett 8:3927-30. 2006
    ..The generation of beta-lactams with two different imines can also be accomplished, providing a method to assemble these products with independent control over five separate substituents...
  9. doi request reprint A direct phosphine-mediated synthesis of pyrroles from acid chlorides and alpha,beta-unsaturated imines
    Yingdong Lu
    Department of Chemistry, McGill University, 801 Sherbrooke Street W, Montreal QC H3A 2K6, Canada
    Org Lett 11:1369-72. 2009
    ..This reaction has been employed to access a diverse range of pyrroles via modulation of the two building blocks and applied as well to the synthesis of lukianol A...
  10. ncbi request reprint A direct, one step synthesis of imidazoles from imines and acid chlorides: a palladium catalyzed multicomponent coupling approach
    Ali R Siamaki
    Department of Chemistry, McGill University, 801 Sherbrooke Street West, Montreal, Quebec H3A 2K6, Canada
    J Am Chem Soc 128:6050-1. 2006
    ..Overall, this catalytic process provides a modular method to prepare imidazoles directly from building blocks that are all either commercially available or readily generated...
  11. doi request reprint Phosphonite mediated 1,3-dipolar cycloaddition: a route to polycyclic 2-pyrrolines from imines, acid chlorides and alkenes
    Marie S T Morin
    Department of Chemistry, McGill University, 801 Sherbrooke St West, Montreal, QC H3A 0B8, Canada
    Chem Commun (Camb) 49:883-5. 2013
    ..The modularity of this reaction can be used to assemble a range of polysubstituted pyrrolines in one pot transformations...
  12. doi request reprint Palladium catalyzed synthesis of münchnones from alpha-amidoethers: a mild route to pyrroles
    Yingdong Lu
    Department of Chemistry, McGill University, 801 Sherbrooke Street W, Montreal QC H3 A 2K6, Canada
    Angew Chem Int Ed Engl 47:5430-3. 2008
  13. ncbi request reprint Copper-catalyzed cross-coupling of imines, acid chlorides, and organostannanes: a multicomponent synthesis of alpha-substituted amides
    Daniel A Black
    Department of Chemistry, McGill University, 801 Sherbrooke Street West, Montreal, Quebec H3A 2K6, Canada
    J Org Chem 70:5133-8. 2005
    ..Use of chloroformates also allows for the formation of N-protected alpha-substituted amines. This chemistry has been applied to the synthesis of isoquinoline alkaloid derivatives through the activation of cyclic imines...
  14. ncbi request reprint Palladium-catalyzed multicomponent coupling of alkynes, imines, and acid chlorides: a direct and modular approach to pyrrole synthesis
    Rajiv Dhawan
    Department of Chemistry, McGill University, 801 Sherbrooke Street West, Montreal, Quebec H3A 2K6, Canada
    J Am Chem Soc 126:468-9. 2004
    ..Mechanistic studies suggest that this process occurs via a complex series of eight individual steps, and this is discussed...
  15. ncbi request reprint Horner-Wadsworth-Emmons reagents as azomethine ylide analogues: pyrrole synthesis via (3 + 2) cycloaddition
    Marie S T Morin
    Department of Chemistry, McGill University, 801 Sherbrooke Street West, Montreal, Quebec H3A 2K6, Canada
    Org Lett 12:4916-9. 2010
    ..The dipoles can be prepared with a diverse range of imines and acid chlorides, and (3 + 2) cycloaddition with unsymmetrical alkynes is highly regiospecific, providing a modular approach to form substituted pyrroles...
  16. ncbi request reprint The development of a catalytic synthesis of münchnones: a simple four-component coupling approach to alpha-amino acid derivatives
    Rajiv Dhawan
    Department of Chemistry, McGill University, 801 Sherbrooke Street West, Montreal, Quebec H3A 2K6, Canada
    J Am Chem Soc 125:1474-5. 2003
    ..The latter represents the first reported catalytic synthesis of alpha-amino acids directly from imine and carbon monoxide building blocks...