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Refereed Publications


43) Parmar, K.; Blaquiere, C.; Gengler, S.; Lukan, B.; Gravel, M. "Synthesis of a Highly Aromatic Cyclopropa-[10]-Annulene", 2020, in preparation.

42) Garapati, V. K. R.; Gravel, M. "Aza-Benzoin Reactions Catalyzed by Oxazolium Salts", 2020, in preparation.

41) Langdon, S. M.; Gravel, M. "An Alternative Method for the Synthesis of N-Pentafluorophenyl Substituted Triazolium Salts", 2020, submitted.

40) Parmar, K.; Haghshenas, P.; Gravel, M. "A Total Synthesis of Hyacinthacine A1 Using a Chemoselective Cross-Benzoin Reaction and a Furan Photooxygenation-Amine Cyclization Strategy", 2020, submitted.

39) Khalkhali, M. R.; Wilde, M. M. D.; Gravel, M. "Enantioselective Stetter Reactions Catalyzed by Bis(amino)cyclopropenylidenes (BACs)", 2019, under revision.

38) 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

37) 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.

36) 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.

35) Haghshenas, P.; Langdon, S. M.; Gravel, M. "Carbene Organocatalysis for Stetter, Benzoin, and Ring-Expansion Reactions", Synlett 2017, 28, 542-559. (invited account) doi

34) 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

33) 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

32) Langdon, S. M. "Imidodiphosphoric acid catalysis", Tetrahedron 2016, 72, 5247-5255. doi

31) 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

30) Wilde, M. M. D.; Gravel, M. "Bis(amino)cyclopropenylidene (BAC) Catalyzed Aza-Benzoin Reaction", Org. Lett. 2014, 16, 5308-5311. doi free e-print

29) 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.

28) Holmes, J. M.; Gravel, M. "The Stetter Reaction" in Comprehensive Organic Synthesis II, G. A. Molander & P. Knochel, Eds.; Elsevier, 2014.

27) 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.

26) 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.

25) 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

23) 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

22) 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

21) 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

20) 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.

19) 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

18) 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

17) 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

16) 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

15) 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


14) 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.

13) 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.

12) 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.

11) 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.

10) 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 U of S:


9) 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

8) Gondi, V.; Gravel, M.; Rawal, V. H. "Hydrogen Bond Catalyzed Enantioselective Vinylogous Mukaiyama Aldol Reaction", Org. Lett. 2005, 7, 5657-5660. doi

7) 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.

6) 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

4) 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

3) 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

2) 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

1) 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