Minnesota State University Moorhead
Dr. Craig P. Jasperse, Chemistry
email: jasperse@mnstate.edu   Phone: (218) 477-2230   Office: Hagen 407J                             

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Jasperse Research

2018:  Medicinal ChemistryResearch: 
Pulmonary Fibrosis
Synthesis of Chemical Library of Antipyrine Analogs
       

Reference
(Scifinder
Usually)

Procedure
Research Overview:  Video            
Antipyrine -Analogs Project Overview-PDF //// DocX
Updated Sept 2018
        test  
Research Group Meeting: 
Jan 13/2016  Video of Same
           
Video Sections Pages Video Time Pod    
Intro-Overview, p1-7      EVERYBODY WATCH 1-7 Vid 42min Pod    
Antipyrine. p8-12.      
A. C4,C5 Variation via Ketoester. (p8, 9)
B. N1-Alkylation. (p10,11)
C. N1-Aldehyde Alkylation-Isomerization (p12)
8-12 Vid 24min Pod Aldehyde-Base Scifinder
Taysir Ald Project Draft 1-docx
 
Acylations, N1 or N2        13-17 Vid min Pod    
N2-Amide Base-Enabled Alkylations       18 Vid min Pod

Project-v1-docx
Some SciFinder

 
N2-Aryl Variations. 
A.  By substituted aryl hydrazines and ketoester       
B.  By Pd-catalyzed Arylation
     
19-20 Vid min Pod    
N2-Methyl by Methylhydrazine and Ketoester        21 Vid min Pod    
C4-Aminomethylation Using Paraformaldehyde     22 Vid min Pod    
Oxidation.  Pyrazolidinones to Pyrazolones 23-24 Vid min Pod    
Sequential Double N1-N2 Alkylation-Acylation using
Aldehyde first, then Acyl Chloride
25 Vid min Pod    
C4-Arylation with Pd(OAc)2 and Ag2CO3 26 Vid min Pod    
C4-Bromination/Iodination/Chlorination 27 Vid min Pod    
C4-Acylamino or 4-Alkylamine Derivatives from Analgin 28 Vid min Pod    
C4-Formylation (scale prep) 29 Vid min Pod    
C4-Iminomethyl analogs.  From the formyl derivative and amine. 30 Vid min Pod    
C5-Dimethyl Pyrazolidinone Analog 31 Vid min Pod Proc-V1.docx  
                 

 

Old Stuff from Years Ago  
Research Projects Overview Movie rtsp://mhdmac.mnstate.edu/~jasperse/CHEM497-Research.mov
How to Load and Watch the Quicktime Movie
Research Projects 2011/2012-PDF Research Projects 2011/2012 Word Version
Research Projects 2009/2010  Research Projects 2009/2010 Word Version
Research Projects 2007 Research Projects 2007 Word Version
Research Projects 2006 Research Projects 2006 Word Version
Summary of Research as of 2006  
 

 

 

 
  Old Publications By Jasperse: Links will Work on MSUM Computers or when Linked to MSUM Library Supporting
Information
OrgLett2009 Nitrile Ylides Cycloadditions-PDF
Nitrile Ylides Cycloadditions-Word
29. Nitrile Ylides: Diastereoselective Cycloadditions Using Chiral Oxazolidinones Without Lewis Acid
Sibi, M. P.; Soeta, T.; Jasperse, C. P.;
Org. Lett.; (Communication); Submitted for Publication.
SI-PDF
SI-Word
JACS2007 Pyrazolidinone Full Paper
28. The Role of Achiral Pyrazolidinone Templates in Enantioselective Diels-Alder Reactions: Scope, Limitations, and Conformational Insights
Sibi, M. P.; Stanley, L. M.; Nie, X.; Venkatraman, L.; Liu, M.; Jasperse, C. P.; J. Am. Chem. Soc.; (Full Paper); 2007; 129(2); 395-405.

SI

 

JACS2005 Nitrile Imine Cycloaddition
27. An Entry to a Chiral Dihydropyrazole Scaffold: Enantioselective [3 + 2] Cycloaddition of Nitrile Imines
Sibi, M. P.; Stanley, L. M.; Jasperse, C. P.;
J. Am. Chem. Soc.; (Communication); 2005; 127(23); 8276-8277.

SI

 

JACS2005 Nitrone Cycloaddition to Cyclopropanes
26. Enantioselective Addition of Nitrones to Activated Cyclopropanes
Sibi, M. P.; Ma, Z.; Jasperse, C. P.;
J. Am. Chem. Soc.; (Communication); 2005; 127(16); 5764-5765.
SI
OrgLett2005 Cycloadditions to Imide Tiglates
25. Enantioselective Cycloadditions with ,-Disubstituted Acrylimides
Sibi, M. P.; Ma, Z.; Itoh, K.; Prabagaran, N.; Jasperse, C. P.;
Org. Lett.; (Communication); 2005; 7(12); 2349-2352.
SI
JACS2004

Nitrile Oxide Cycloadditions
24. Chiral Lewis Acid Catalysis in Nitrile Oxide Cycloadditions
Sibi, M. P.; Itoh, K.; Jasperse, C. P.;
J. Am. Chem. Soc.; (Communication); 2004; 126(17); 5366-5367.

SI
JACS2004 Nitrone Cycloadditions
23. Exo Selective Enantioselective Nitrone Cycloadditions
Sibi, M. P.; Ma, Z.; Jasperse, C. P.;
J. Am. Chem. Soc.; (Communication); 2004; 126(3); 718-719.
SI
JACS 2003 Hydroxylamine Addition to Tiglates 22. Enantioselective Synthesis of alpha,beta-Disubstituted-beta-amino Acids. Sibi, Mukund P.; Prabagaran, Narayanasamy; Ghorpade, Sandeep G.; Jasperse, Craig P.. Journal of the American Chemical Society (2003), 125(39), 11796-11797. SI
JEuroChem2002 Chiral Relay Review 21. Chiral relay: A novel strategy for the control and amplification of enantioselectivity in chiral Lewis acid promoted reactions. Corminboeuf, Olivier; Quaranta, Laura; Renaud, Philippe; Liu, Mei; Jasperse, Craig P.; Sibi, Mukund P. Chemistry--A European Journal (2003), 9(1), 28-35.  
JACS 2002 Double Diastereoselection in Radical Additions 20. Acyclic Diastereoselection in Prochiral Radical Addition to Prochiral Olefins. Sibi, Mukund P.; Rheault, Tara R.; Chandramouli, Sithamalli V.; Jasperse, Craig P.. Journal of the American Chemical Society (2002), 124(12), 2924-2930. SI
Comptes Rendus de l'Academie des Sciences, Serie IIc: Chimie 2001 Annulation Paper. 19. Highly diastereoselective radical addition-cyclization strategy: facile synthesis of substituted furans. Sibi, Mukund P.; Rheault, Tara R.; Miyabe, Hideto; Patil, Kalyani; Jasperse, Craig P.. Comptes Rendus de l'Academie des Sciences, Serie IIc: Chimie (2001), 4(7), 581-584.  
JACS 2001 Original Chiral Relay Paper: Diels-Alder with Copper 18. A new approach to enantiocontrol and enantioselectivity amplification: chiral relay in Diels-Alder reactions. Sibi, Mukund P.; Venkatraman, Lakshmanan; Liu, Mei; Jasperse, Craig P.. Journal of the American Chemical Society (2001), 123(34), 8444-8445. SI
JACS 1999 Full Diastereoselective Radical Paper 17. Free radical-mediated intermolecular conjugate additions. Effect of the Lewis acid, chiral auxiliary, and additives on diastereoselectivity. Sibi, Mukund P.; Ji, Jianguo; Sausker, Justin B.; Jasperse, Craig P.. Journal of the American Chemical Society (1999), 121(33), 7517-7526. SI
JACS 1998 Original Enantioselective Beta-Amino Acid Paper 16. Chiral Lewis Acid Catalysis in Conjugate Additions of O-Benzylhydroxylamine to Unsaturated Amides. Enantioselective Synthesis of _-Amino Acid Precursors. Sibi, Mukund P.; Shay, John J.; Liu, Mei; Jasperse, Craig P.. Journal of the American Chemical Society (1998), 120(26), 6615-6616. SI
JACS 1995 Diastereoselective Radical Paper 15. Lewis acid-mediated intermolecular _-selective radical additions to N-enoyloxazolidinones. Sibi, Mukund P.; Jasperse, Craig P.; Ji, Jianguo. Journal of the American Chemical Society (1995), 117(43), 10779-80. SI

Older Publications By Jasperse

Synlett, 1992, 943-961 14. New mechanistic insights into reductions of halides and radicals with samarium(II) iodide. Curran, Dennis P.; Fevig, Thomas L.; Jasperse, Craig P.; Totleben, Michael J. Synlett (1992), (12), 943-61.
Synlett, 1992, 25-26 13. Radical isomerization and allylation reactions of 2-iodo-3,3-dimethyl-4-pentenoate esters. Curran, Dennis P.; Jasperse, Craig M.; Abraham, Ann C. Synlett (1992), (1), 25-6.
JOC 1991 Absolute Rate Constants for Vinyl and Aryl Radicals12. Approximate absolute rate constants for the reactions of tributyltin radicals with aryl and vinyl halides. Curran, Dennis P.; Jasperse, Craig P.; Totleben, Michael J. Journal of Organic Chemistry (1991), 56(25), 7169-72.
Chem Reviews 1991 Radical Reactions in Natural Product Synthesis 11. Radical reactions in natural product synthesis. Jasperse, Craig P.; Curran, Dennis P.; Fevig, Thomas L. Chemical Reviews (1991), 91(6), 1237-86.
JACS 1990 Total Synthesis of Modhephene using Radical Chemistry 10. Sequential radical cyclization approach to propellane triquinanes. Total synthesis of (_)-modhephene. Jasperse, Craig P.; Curran, Dennis P. Journal of the American Chemical Society (1990), 112(14), 5601-9.
INCH 1990 Carborane Cluster Chemistry 9. Substituent effects in cluster species. 6. Photoelectron spectra of 5- and 5,6-substituted 2,4-dicarba-closo-heptaborane(7). Beltram, G. A.; Jasperse, C.; Cavanaugh, M. A.; Fehlner, T. P. Inorganic Chemistry (1990), 29(2), 329-35.
JOC 1988 Synthesis and Characterisation of the First Stable Selenenic Acid 8. Organoselenium chemistry. Preparation and reactions of 2,4,6-tri-tert-butylbenzeneselenenic acid. Reich, Hans J.; Jasperse, Craig P.. Journal of Organic Chemistry (1988), 53(10), 2389-90.
JACS 1987 Redox chemistry of a Selenocysteine Model System 7. Organoselenium chemistry. Redox chemistry of selenocysteine model systems. Reich, Hans J.; Jasperse, Craig P.. Journal of the American Chemical Society (1987), 109(18), 5549-51.
JOC 1986 Enolate Alkylations of Bromomethylselenides 6. Organoselenium chemistry. Alkylation of acid, ester, amide, and ketone enolates with bromomethyl benzyl selenide and sulfide. Preparation of selenocysteine derivatives. Reich, Hans J.; Jasperse, Craig P.; Renga, James M. Journal of Organic Chemistry (1986), 51(15), 2981-8.
J Molecular Structure 1983 5. On the structures of H+(CO)5 and H+(N2)5. DeKock, Roger L.; Jasperse, Craig P.. THEOCHEM (1983), 14(1-2), 231-2.
INCH 1983 Proton Affinities for Borane and Carborane Clusters 4. MNDO studies of proton affinity as a probe of electronic structure. 2. Boranes and carboranes. DeKock, Roger L.; Jasperse, Craig P.. Inorganic Chemistry (1983), 22(26), 3843-8.
INCH 1983 MNDO Studies of Proton Affinities 3. MNDO studies of proton affinity as a probe of electronic structure. 1. General overview. DeKock, Roger L.; Jasperse, Craig P.. Inorganic Chemistry (1983), 22(26), 3839-43.
J Molecular Structure 1983 2. Quantum chemical calculations on the structure of chlorine fluoride ((Cl2F)+) and related molecules. Dekock, Roger L.; Jasperse, Craig P.; Dao, Daniel T.; Bieda, James H.; Liebman, Joel F. Journal of Fluorine Chemistry (1983), 22(6), 575-84.
J Molecular Structure 1983 1. MNDO study of the proton affinity of fluorinated formaldehydes and acetones. DeKock, Roger L.; Jasperse, Craig P.; Konings, Mark S. THEOCHEM (1983), 11(3-4), 343-50.

Patents By Jasperse

Patent 2003 1. Provisional Patent: Beta-Amino Acids and Methods and Intermediates for Making Same. Sibi, Mukund P,; Jasperse, Craig P.; Prabagaran, Narayansamy; Ghorpade, Sandeep. Provisional patent application Docket No. 047.00040(RFT-112).
Patent 2003 2. Provisional Patent: Chiral Ligands with Fluxional Groups. Sibi, Mukund P.; Manyem, Shankar; Jasperse, Craig Peter; Zhang, Ruzhou. Provisional patent application Registration No. 38,601, Docket No. 047.000300(RFT-114), Date: 18-June-2003
Patent 2002 3. Pyrazole Intermediates in a Method of Preparation of Beta-Amino Acids. Sibi, Mukund P.; Shay, John Joseph; Jasperse, Craig Peter; Liu, Mei. Patent Number 6,191,283, issue date 2/20/2001.
Patent 2000 4. Method of preparation of Beta-amino acids. Sibi, Mukund P.; Shay, John Joseph; Jasperse, Craig Peter; Liu, Mei. U.S. (2000), 11 pp. Patent Number 6,0809,857, issue date 6/27/2000

Recent Publications: Not by Jasperse, but of Significant Relavance
Metal Triflimides
Link to Sibi Homepage and Sibi Publication List

Enantioselective Free Radical Additions: Sibi/Porter Review, Accounts Chemical Research 1999
Mei's Original Hydroxylamine Addition-OrgLet2000
Mei's Chiral Relay Paper: Hydroxylamine with Magnesium-Org Lett2001
Ji's Optimized Enantioselective Radical Addition-JOC 1997
Ji's and Porter's Original Enantioselective Radical Addition-JACS1996
Ji's Tandem Addition-Allylation on AcrylatesJOC96

Chen's Tandem Radical Alkylation Paper-JACS2001

Jacobsen Hydrazoic Acid Addition to Imides-JACS1999