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Sunil Pansare

Sunil Pansare
Office: C4016
Phone: 709-864-8535
Email (@mun.ca):
Post: Department of Chemistry
Memorial University of Newfoundland
St. John's, NL A1B 3X7 CANADA

The development of expedient asymmetric routes to functionalized organic molecules is of interest because most chiral, biologically relevant molecules are optimally active as single enantiomers.

Our research interests are mainly in the area of asymmetric organic synthesis. We have developed organocatalytic variants of conjugate addition reactions and vinylogous aldol reactions, and we have applied our methodology in the total synthesis of a variety of alkaloids. We have also utilized ephedrine as a chiral controller in the asymmetric synthesis of alpha hydroxy acids and applied this methodology in the synthesis of alkaloids and marine natural products. Other synthetic methodologies developed in our group include new applications of sulfamide in the synthesis of vicinal diamines and related heterocycles and the hetero atom-H bond insertion reactions of diazocarbonyl compounds. We have identified scandium triflate as a promising catalyst for the insertion reactions. Recent research in our group focuses on the design of new organocatalysts for fundamental, carbon-carbon bond forming reactions. We are also interested in the development of new multicomponent reactions for combinatorial chemistry based applications in diversity-oriented synthesis.

Current research projects include

    Asymmetric, organocatalytic carbon-carbon bond forming reactions, e.g. Michael, aldol and nitroaldol (Henry) reactions.

    Asymmetric synthesis of functionalized pyrrolidines, indolizidines and quinolizidines

    Asymmetric synthesis of substituted hydroxy amino acid motifs (peptide isosteres).

    Lewis acid-mediated asymmetric diazocarbonyl insertion reactions into N-H and O-H bonds.

    Synthesis of highly functionalized mono- and bicyclic scaffolds for diversity oriented synthesis.

Selected publications

Cooze, C.; Manchoju, A.; Pansare, S. V. Synthesis of (–)-Muricatacin and (–)-(R,R)-L-Factor Involving an Organocatalytic Direct Vinylogous Aldol Reaction Synlett 2017, DOI: 10.1055/s-0036-1590858 (Special issue in honor of Professor Victor Snieckus)

Manchoju, A.; Pansare, S. V. Catalytic Undirected Intermolecular C−H Functionalization of Arenes with 3‑Diazofuran-2,4-dione: Synthesis of 3‑Aryl Tetronic Acids, Vulpinic Acid, Pinastric Acid, and Methyl Isoxerocomate Org. Lett. 2016, 18, 5952.

Gopinathan, M.; Pansare, S. V. Modular Synthesis of Allyl Vinyl Ethers for the Enantioselective Construction of Functionalized Quaternary Stereocenters RSC Adv. 2016, 6, 104556.

Moorthy, N. V. G.; Dyapa, R.; Pansare, S. V. Formal Synthesis of (+)-Lasubine II and (-)-Subcosine II via Organocatalytic Michael Addition of a Ketone to an alpha-Nitrostyrene Org. Lett. 2015, 17, 5312.

Manchoju, A.; Thorat, R. G.; Pansare, S. V. Enantioselective Synthesis of Functionalized Quaternary Stereocenters Eur. J. Org. Chem. 2015, 5939.

Pansare, S. V.; Thorat, R. G. Recent Advances in the Synthesis of Selected Indolizidine and Quinolizidine Alkaloids Targets in Heterocyclic Systems 2013, 17, 57.

Thorat, R. G.; Pansare, S. V. A General Approach to 1-Hydroxymethylquinolizidine and 8-Hydroxymethylindolizidine Stereoisomers: Synthesis of (+)-Epitashiromine and Formal Syntheses of (+)-Epilupinine and (+)-Tashiromine Eur. J. Org. Chem. 2013, 7282.

Pansare, S. V.; Kulkarni, K. G. An enantioselective approach to (-)-aphanorphine featuring a stereoselective oxidative amidation RSC Advances 2013, 3, 19127.

Pansare, S. V.; Paul, E. K. Synthesis of Synthesis of (+)-Febrifugine and a Formal Synthesis of (+)-Halofuginone Employing an Organocatalytic Direct Vinylogous Aldol Reaction Synthesis 2013, 45, 1863. (Special issue in honor of Professor Scott Denmark)
(Featured on the Organic Chemistry portal (www.organic-chemistry.org/Highlights/2014/12May.shtm)

Pansare, S. V.; Dyapa, R. Enantioselective Approach to Functionalized Quinolizidines: Synthesis of (+)-Julandine and (+)-Cryptopleurine Org. Biomol. Chem. 2012, 10, 6776.

Pansare, S. V.; Paul, E. K. Synthesis of (+)-L-733,060, (+)-CP-99,994 and (2S,3R)-3-Hydroxypipecolic acid: Application of an Organocatalytic direct vinylogous aldol reaction Org. Biomol. Chem. 2012, 10, 2119.

Pansare, S. V.; Paul, E. K. The Organocatalytic Vinylogous Aldol Reaction: Recent Advances Chem. Eur. J. 2011, 17, 8770.
(Among the top 20 most cited Minireviews in 'Chemistry—A European Journal' in the past 20 years)

Pansare, S. V.; Lingampally, R.; Dyapa, R. A Simple Enantioselective Route to Functionalized Indolizidines: Synthesis of (+)-Ipalbidine and (+)-Antofine Eur. J. Org. Chem. 2011, 2235.

Pansare, S. V.; Paul, E. K. Organocatalytic Asymmetric Direct Vinylogous Aldol Reactions of g-Crotonolactone with Aromatic Aldehydes Chem. Commun. 2011, 47, 1027.

Pansare, S. V.; Adsool, S. V.; Dyapa, R. Enantioselective Synthesis of (S) - Homocitric Acid Lactone and (R) - Per Homocitric Acid Lactone Involving Organocatalysis Tetrahedron: Asymmetry 2010, 21, 771.

Pansare, S. V.; Lingampally, R.; Kirby, R. L. Stereoselective Synthesis of 3-Aryloctahydroindoles and Application in a Formal Synthesis of (-)-Pancracine Org. Lett. 2010, 12, 556.
(Highlighted in Synfacts 2010, 3, 354)

Pansare, S. V.; Kirby, R. L. Secondary-Secondary Diamine Catalysts for the Enantioselective Michael Addition of Cyclic Ketones to Nitroalkenes Tetrahedron 2009, 65, 4557.

Pansare, S. V.; Lingampally, R. Synthesis and Evaluation of Guanidinyl Pyrrolidines as Bifunctional Catalysts for Enantioselective Conjugate Additions to Cyclic Enones Org. Biomol. Chem. 2009, 7, 319.
(In OBC Top 10 articles, January 2009)

Adsool, V. A.; Pansare, S. V. An Enantioselective Approach to (+)-Laurencin Org. Biomol. Chem. 2008, 6, 2011.

Pansare, S. V.; Adsool, V. A. Enantioselective Synthesis of (R)-Homocitric Acid Lactone Tetrahedron Lett. 2007, 48, 7099.

Pansare, S. V.; Adsool, V. A. Enantioselective Synthesis of Functionalized Medium-Sized Oxacycles Org. Lett. 2006, 8, 5897.

Pansare, S. V.; Pandya, K. Simple Diamine- and Triamine-Protonic Acid Catalysts for the Enantioselective Michael Addition of Cyclic Ketones to Nitroalkenes J. Am. Chem. Soc. 2006, 128, 9624.
(JACS Hot Paper, May 2007)

Pansare, S. V.; Adsool, V. A. A Concise, Enantioselective Approach to (-)-Quinic Acid Org. Lett. 2006, 8, 2035.