Refereed Publications


  1. Garapati, V. K. R.; Gravel, M. "Aza-Benzoin Reactions Catalyzed by Oxazolium Salts", 2020, in preparation. (no, really, it's true)
  2. Ji, T.; Garapati, V. K. R.; Gravel, M. "A Purification-Free Method for the Synthesis of Thiazolium Salts Using P2S5-Py2 Complex or P4S10", Can. J. Chem., re-submitted after revision.  pre-print
  3. Parmar, K.; Blaquiere, C. S.; Lukan, B. E.; Gengler, S. N.; Gravel, M. "Is Schleyer’s Predicted All-Cis [10]Annulene an Unstable Framework?", J. Am. Chem. Soc., re-submitted after revision.  pre-print
  4. Parmar, K.; Gravel, M. "Quantifying Vertical Resonance Energy in Aromatic Systems with Natural Bond Orbitals", Eur. J. Org. Chem., in print. (selected as Very Important Paper) doi  pre-print
  5. Rowshanpour, R.; Gravel, M.; Dudding, T. "N-Heterocyclic Carbene Organocatalyzed Redox-Active/Ring-Expansion Reactions: Mechanistic Insights Unveiling Base Cooperativity", J. Org. Chem. 2022, 87, 16785-16793.  doi
  6. Langdon, S. M.; Gravel, M. "An Alternative Method for the Synthesis of N-Pentafluorophenyl Triazolium Salts", Org. Lett. 2022, 24, 7168-7172.  doi
  7. Parmar, K.; Blaquiere, C. S.; Lukan, B. E.; Gengler, S. N.; Gravel, M. "Synthesis of a highly aromatic and planar dehydro [10]annulene derivative", Nat. Synth. 2022, 1, 696-700.  doi  free version  pre-print. Chosen as Synfacts of the Month.
  8. Parmar, K.; Haghshenas, P.; Gravel, M. "Total Synthesis of (+)-Hyacinthacine A1 Using a Chemoselective Cross-Benzoin Reaction and a Furan Photooxygenation–Amine Cyclization Strategy", Org. Lett. 2021, 23, 1416-1421.  doi
  9. Khalkhali, M. R.; Wilde, M. M. D.; Gravel, M. "Enantioselective Stetter Reactions Catalyzed by Bis(amino)cyclopropenylidenes: Important Role for Water as an Additive", Org. Lett. 2021, 23, 155-159.  doi  Highlighted on the  Organic Chemistry Portal.
  10. Duan, A.; Fell, J. S.; Peiyuan, Y.; Lam, C. Y.-h.; Gravel, M.; Houk, K. N. "Theoretical Study of Diastereoselective NHC-Catalyzed Cross-Benzoin Reactions between Furfural and N-Boc-Protected a-Amino Aldehydes", J. Org. Chem. 2019, 84, 13565-13571.  doi
  11. Langdon, S. M.; Parmar, K.; Wilde, M. M. D.; Gravel, M. "Benzoin Reaction" in  N-Heterocyclic Carbenes in Organocatalysis , A. T. Biju, Ed.; Wiley-VCH, 2019.
  12. Garapati, V. K. R.; Gravel, M. "Oxazolium Salts as Organocatalysts for the Umpolung of Aldehydes", Org. Lett. 2018, 20, 6372-6375.  doi   free e-print . Highlighted on the  Organic Chemistry Portal .
  13. Haghshenas, P.; Langdon, S. M.; Gravel, M. "Carbene Organocatalysis for Stetter, Benzoin, and Ring-Expansion Reactions", Synlett 2017, 28, 542-559. (invited account)  doi
  14. Haghshenas, P.; Gravel, M. "Substrate-Controlled Diastereoselectivity Reversal in NHC-Catalyzed Cross-Benzoin Reactions Using N-Boc-N-Bn-Protected α-Amino Aldehydes", J. Org. Chem. 2016, 81, 12075-12083.  doi   free e-print
  15. Haghshenas, P.; Gravel, M. "Chemo- and Diastereoselective N-Heterocyclic Carbene-Catalyzed Cross-Benzoin Reactions Using N-Boc-α-amino Aldehydes", Org. Lett. 2016, 18, 4518-4521.  doi   free e-print
  16. Langdon, S. M. "Imidodiphosphoric acid catalysis", Tetrahedron 2016, 72, 5247-5255.  doi
  17. Langdon, S. M.; Legault, C. Y.; Gravel, M. "Origin of Chemoselectivity in N-Heterocyclic Carbene-Catalyzed Cross-Benzoin Reactions: DFT and Experimental Insights",  J. Org. Chem. 2015, 80, 3597-3610.  doi   free e-print
  18. Wilde, M. M. D.; Gravel, M. "Bis(amino)cyclopropenylidene (BAC) Catalyzed Aza-Benzoin Reaction",  Org. Lett. 2014, 16, 5308-5311.  doi   free e-print
  19. Langdon, S. M.; Wilde, M. M. D.; Thai, K.; Gravel, M. "Chemoselective N-Heterocyclic Carbene-Catalyzed Cross-Benzoin Reactions: Importance of the Fused Ring in Triazolium Salts", J. Am. Chem. Soc. 2014, 136, 7539-7542.  doi   free e-print . This article was highlighted in  Synfacts .
  20. Holmes, J. M.; Gravel, M. "The Stetter Reaction" in  Comprehensive Organic Synthesis II , G. A. Molander & P. Knochel, Eds.; Elsevier, 2014.
  21. Wilde, M. M. D.; Gravel, M. "Bis(amino)cyclopropenylidenes as Organocatalysts for Acyl Anion and Extended Umpolung Reactions", Angew. Chem. Int. Ed. 2013, 52, 12651-12654. (Hot Paper)  doi . This article is the object of a very nice highlight in  Angew. Chem. Int. Ed.  and one in  Synfacts .
  22. Thai, K.; Langdon, S. M.; Bilodeau, F.; Gravel, M. "Highly Chemo- and Enantioselective Cross-Benzoin Reaction of Aliphatic Aldehydes and α-Ketoesters", Org. Lett. 2013, 15, 2214-2217.  doi   free e-print . This article was highlighted on the  Organic Chemistry Portal .
  23. Thai, K.; Sánchez-Larios, E.; Gravel, M. "Carbene Catalysts" in  Comprehensive Enantioselective Organocatalysis , P. I. Dalko, Ed.; Wiley-VCH, 2013.
  24. Zhou, S.; Sánchez-Larios, E.; Gravel, M. "Scalable Synthesis of Highly Reactive 1,3-Diaminodienes from Vinamidinium Salts and Their Use in Diels-Alder Reactions", J. Org. Chem. 2012, 77, 3576-3582.  doi   free e-print
  25. Sánchez-Larios, E.; Thai, K.; Bilodeau, F.; Gravel, M. "Highly Enantioselective Intermolecular Stetter Reactions of β-Aryl Acceptors: α-Ketoester Moiety as Handle for Activation and Synthetic Manipulations",  Org. Lett. 2011, 13, 4942-4945.  doi   free e-print
  26. Sánchez-Larios, E.; Holmes, J. M.; Daschner, C. L.; Gravel, M. "Synthesis of Spiro Bis-Indanes via Domino Stetter-Aldol-Michael and Stetter-Aldol-Aldol Reactions: Scope and Limitations", Synthesis 2011, 1896-1904. (invited article)  doi
  27. Sánchez-Larios, E.; Holmes, J. M.; Daschner, C. L.; Gravel, M. "NHC-Catalyzed Spiro Bis-Indane Formation via Domino Stetter-Aldol-Michael and Stetter-Aldol-Aldol Reactions", Org. Lett. 2010 , 12, 5772-5775.  doi   free e-print
  28. Thai, K.; Wang, L.; Dudding, T.; Bilodeau, F.; Gravel, M. "NHC-Catalyzed Intramolecular Redox Amidation for the Synthesis of Functionalized Lactams", Org. Lett. 2010, 12, 5708-5711.  doi   free e-print . This article was highlighted in  Synfacts  and on the  Organic Chemistry Portal .
  29. Thai, K.; Gravel, M. "Design, Synthesis, and Application of Chiral Electron-Poor Guanidines as Hydrogen-Bonding Catalysts for the Michael Reaction", Tetrahedron: Asymmetry 2010, 21, 751-755.  doi
  30. Thai, K.; Clement, C. W.; Gravel, M. "A Simple One-Pot Synthesis of Triflyl Guanidines: Access to Highly Substituted Electron-Poor Guanidines", Tetrahedron Lett. 2009, 50, 6540-6542.  doi
  31. Sánchez-Larios, E.; Gravel, M. "Diastereoselective Synthesis of Indanes via a Domino Stetter-Michael Reaction", J. Org. Chem. 2009, 74, 7536-7539.  doi   free e-print
  32. Holmes, J. M.; Albert, A. L.; Gravel, M. "Practical Synthesis and Highly Diastereoselective Diels-Alder Reactions of 1-Alkylthio-3-silyloxybutadienes", J. Org. Chem. 2009, 74, 6406-6409.  doi   free e-print
  33. Wang, L.; Thai, K.; Gravel, M. "NHC-Catalyzed Ring Expansion of Oxacycloalkane-2-Carboxaldehydes: A Versatile Synthesis of Lactones", Org. Lett. 2009, 11, 891-893.  doi   free e-print . This article was highlighted in  Synfacts  and on the  Organic Chemistry Portal .

Monographs

  1. Haghshenas, P.; Gravel, M. "3-Benzyl-5-(2-hydroxyethyl)-4-methyl-1,3-thiazolium Chloride" dans  Encyclopedia of Reagents for Organic Synthesis (e-EROS) , D. Crich, Ed.-in-chief; John Wiley & Sons, 2016.
  2. Langdon, S. M.; Gravel, M. "1,2,4-Triazolo[4,3-a]pyridinium,5,6,7,8-tetrahydro-2-(2,3,4,5,6-pentafluorophenyl)-, Tetrafluoroborate" dans  Encyclopedia of Reagents for Organic Synthesis (e-EROS) , D. Crich, Ed.-in-chief; John Wiley & Sons, 2016.
  3. Wilde, M. M.; Gravel, M. "1,2-Bis(diethylamino)cyclopropenium Tetraphenylborate" dans  Encyclopedia of Reagents for Organic Synthesis (e-EROS) , D. Crich, Ed.-in-chief; John Wiley & Sons, 2016.
  4. Wilde, M. M.; Gravel, M. "(2-Acetylamino)propanedioic Acid" in  Encyclopedia of Reagents for Organic Synthesis (e-EROS) , D. Crich, Ed.-in-chief; John Wiley & Sons, 2013.
  5. Sánchez-Larios, E.; Gravel, M. "Lithium Hydroperoxide" update in  Encyclopedia of Reagents for Organic Synthesis (e-EROS) , D. Crich, Ed.-in-chief; John Wiley & Sons, 2011.

Prior to USask

  1. Turkmen, Y. E.; Gravel, M.; Rawal, V. H. "Studies Directed toward the Synthesis of Aspidophytine: Construction of Its Perhydroquinoline Core",  J. Org. Chem.   2016 ,  81 , 10454–10462.  doi   free e-print
  2. Gondi, V.; Gravel, M.; Rawal, V. H. "Hydrogen Bond Catalyzed Enantioselective Vinylogous Mukaiyama Aldol Reaction",  Org. Lett.   2005 ,  7 , 5657-5660.  doi
  3. Gravel, M.; Touré, B. B.; Hall, D. G. "Practical procedure for the preparation of functionalized (E)-1-alkenylboronic acids including the unprecedented 1-alkoxycarbonyl derivatives",  Org. Prep. Proc. Int.   2004 ,  36 , 573-579.
  4. Gravel, M.; Lachance, H.; Lu, X.; Hall, D. G. "Scope and limitations of the scandium-catalyzed enantioselective addition of chiral allylboronates to aldehydes",  Synthesis   2004 , 1290-1302. (Feature Article)  doi
  5. Lachance, H.; Lu, X.; Gravel, M.; Hall, D. G. "Scandium-Catalyzed Allylboration of Aldehydes as a Practical Method for Highly Diastereo- and Enantioselective Construction of Homoallylic Alcohols",  J. Am. Chem. Soc.   2003 ,  125 , 10160-10161.  doi
  6. Gravel, M.; Thompson, K. A.; Zak, M.; Bérubé, C.; Hall, D.G. "Universal Solid Phase Approach for the Immobilization, Derivatization, and Resin-to-Resin Transfer Reactions of Boronic Acids"  J. Org. Chem.   2002 ,  67 , 3-15.  (Article featured on cover page)   doi
  7. Gravel, M.; Bérubé, C. D.; Hall, D. G. "Resin-to-Resin Suzuki Coupling of Solid Supported Arylboronic Acids"  J. Comb. Chem.   2000 ,  2 , 228-231.  doi
  8. Hall, D. G.; Tailor, J.; Gravel, M. "N,N-Diethanolaminomethyl Polystyrene: An Efficient Solid Support to Immobilize Boronic Acids"  Angew. Chem., Int. Ed.   1999 ,  38 , 3064-3067.  doi
  9. Déziel, R.; Malenfant, É.; Thibault, C.; Fréchette, S.; Gravel, M. "2,6-Bis[(2S)-Tetrahydrofuran-2-yl]phenyl Diselenide: An Effective Reagent for Asymmetric Electrophilic Addition Reactions to Olefins"  Tetrahedron Lett.   1997 ,  38 , 4753-4756.  doi