Publications: Friestad Group

Peer-Reviewed Publications

43. Friestad, G. K.; Lee, H. J. "Trans-2,5-Disubstituted Tetrahydrofurans via Additions of Carbon Nucleophiles to the Strained Bicyclic Acetal 2,7-Dioxabicyclo[2.2.1]heptane." Org. Lett. 2009, 11, 3958-3961.  [PDF]

42. Friestad, G. K.; Banerjee, K. "Synthesis of gamma-Amino Esters via Mn-Mediated Radical Addition to Chiral gamma-Hydrazonoesters." Org. Lett. 2009, 11, 1095-1098. [PDF]

41. Friestad, G. K.; Wu, Y. "Intermolecular Non-Reductive Alkylation of Enamides via Radical-Polar Crossover." Org. Lett. 2009, 11, 819-822. [PDF]

40. Friestad, G. K. "Reaction of Acetals with Organometallic Reagents." in Science of Synthesis, Vol. 40a: Compounds with One Saturated Carbon-Heteroatom Bond: Amines and Ammonium Salts, Enders, D.; Shaumann, E., Eds.; Thieme: Stuttgart, Germany, 2009, pp. 91-110.

39. Friestad, G. K. "Addition of Carbanions to Azomethines." in Science of Synthesis, Vol. 40a: Compounds with One Saturated Carbon-Heteroatom Bond: Amines and Ammonium Salts, Enders, D.; Shaumann, E., Eds.; Thieme: Stuttgart, Germany, 2009, pp 305-342.

38. Friestad, G. K.; Jiang, T.; Fioroni, G. M. "Stereocontrol in Radical Mannich Equivalents for Aminosugar Synthesis: Haloacetal and 2-(Phenylthio)vinyl Tethered Radical Additions to alpha-Hydroxyhydrazones." Tetrahedron 2008, 64, 11549-11557.  [PDF]

37. Friestad, G. K.; Ji, A. "Mn-Mediated Coupling of Alkyl Iodides and Ketimines: A Radical Addition Route to alpha,alpha-Disubstituted alpha-Aminoesters" Org. Lett. 2008, 10, 2311-2313.  [PDF]

36. Korapala, C. S.; Qin, J.; Friestad, G. K. "Quinine Synthesis Studies: A Radical-Ionic Annulation via Mn-Mediated Addition to Chiral N-Acylhydrazones" Org. Lett. 2007, 9, 4243-4246.  [PDF]

35. Friestad, G. K.; Mathies, A. K. "Effects of alpha-Alkoxy Substitution and Conformational Constraints on 6-exo Radical Cyclizations of Hydrazones via Reversible Thiyl and Stannyl Additions." Tetrahedron 2007, 63, 9373-9381.  [PDF]

34. Friestad, G. K.; Jiang, T.; Mathies, A. K. "Enhanced Reactivity in Radical Cyclizations of Hydrazones Using the Silicon-Tethered 1-Bromovinyl Group." Tetrahedron 2007, 63, 3964-3972.  [PDF]

33. Friestad, G. K.; Jiang, T.; Mathies, A. K. "Aldehyde-Selective Wacker Oxidation in a Thiyl-Mediated Vinyl Group Transfer Route to Daunosamine." Org. Lett. 2007, 9, 777-780.  [PDF]

32. Friestad, G. K.; Mathies, A. K. "Recent Developments in Asymmetric Catalytic Addition to C=N Bonds." Tetrahedron 2007, 63, 2541-2569.   [PDF]
(#7 most downloaded article in Tetrahedron for the year 2007; Top 50 Most Cited Articles in Tetrahedron for the years 2006-2009)

31. Friestad, G. K.; Qin, J.; Suh, Y.; Marié, J.-C. "Mn-Mediated Coupling of Alkyl Iodides and Chiral N-Acylhydrazones: Optimization, Scope, and Evidence for a Radical Mechanism."  J. Org. Chem. 2006, 71, 7016-7027.  [PDF]

30. Ding, H.; Friestad, G. K. "Strecker Reactions of Chiral N-Acylhydrazones." Heterocycles 2006, 70, 185-199.

29. Friestad, G. K.; Korapala, C. S.; Ding, H.  "Dual Activation in Asymmetric Allylsilane Addition to Chiral N-Acylhydrazones: Method Development, Mechanistic Studies, and Elaboration of Homoallylic Amine Adducts." J. Org. Chem. 2006, 71, 281-289.  [PDF]

28. Ding, H.; Friestad, G. K.  "Asymmetric Addition of Allylic Nucleophiles to Imino Compounds."  Synthesis 2005, 2815-2829. 

27. Friestad, G. K.; Draghici, C.; Soukri, M.; Qin, J. "Radical Addition Approach to Asymmetric Amine Synthesis: Design, Implementation, and Comparison of New Chiral N-Acylhydrazones." J. Org. Chem. 2005, 70, 6330-6338.   [PDF]

26. Friestad, G. K.  "Chiral N-Acylhydrazones: Versatile Imino Acceptors for Asymmetric Amine Synthesis."  Eur. J. Org. Chem. 2005, 3157-3172. 
(#1 most read article in Eur. J. Org. Chem. for July 2005)

25. Friestad, G. K.; Fioroni, G. M.  "Haloacetal Radical Cyclizations of alpha- and beta-Hydroxyhydrazones."  Org. Lett. 2005, 7, 2393-2396.  [PDF]

24. Friestad, G. K.; Deveau, A. M.; Marié, J.-C. "Stereoselective Mn-Mediated Coupling of Functionalized Iodides and Hydrazones: A Synthetic Entry to the Tubulysin gamma-Amino Acids" Org. Lett. 2004, 6, 3249-3252.   [PDF]

23. Ding, H.; Friestad, G. K. "Allyltrimethoxysilane Addition to N-Acylhydrazones:  Two Catalytic Methods Employing CuCl and Fluoride." Synthesis 2004, 2216-2221. 

22. Friestad, G. K.; Jiang, T.; Mathies, A. K.; Massari, S. E. "Silicon-Containing Heterocycles in Stereocontrolled Radical Additions to Chiral Hydrazones." Phosphorous, Sulfur, and Silicon 2004, 179, 955-956.

21. Ding, H.; Friestad, G. K. "Trifluoroacetyl-Activated Nitrogen-Nitrogen Bond Cleavage of Hydrazines by Samarium (II) Iodide." Org. Lett. 2004, 6, 637-640.  [PDF]

20. Friestad, G. K.; Massari, S. E.  "A Silicon Tether Approach for Addition of Functionalized Radicals to Chiral alpha-Hydroxyhydrazones: Diastereoselective Additions of Hydroxymethyl and Vinyl Synthons." J. Org. Chem. 2004, 69, 863-875.  [PDF]

19. Friestad, G. K.; Shen, Y.; Ruggles, E. L. "Enantioselective Radical Addition to N-Acylhydrazones Mediated by Chiral Lewis Acids." Angew. Chem. Int. Ed. 2003, 42, 5061-5063. 

18. Friestad, G. K.; Jiang, T.; Fioroni, G. M.  "Tandem Thiyl Radical Addition and Cyclization of Chiral Hydrazones Using a Silicon-Tethered Alkyne." Tetrahedron: Asymmetry 2003, 14, 2853-2856. 

17. Qin, J.; Friestad, G. K. "Stereocontrol in Hydride Addition to Ketone-Derived Chiral N-Acylhydrazones." Tetrahedron 2003, 59, 6393-6402. 

16. Shen, Y.; Friestad, G. K. "Comparison of Electrophilic Amination Reagents for N-Amination of 2-Oxazolidinones and Application to Synthesis of Chiral Hydrazones." J. Org. Chem. 2002, 67, 6236-6239.   [PDF]

15. Friestad, G. K.; Ding, H. "Asymmetric Allylsilane Additions to Enantiopure N-Acylhydrazones with Dual Activation by Fluoride and In(OTf)3." Angew. Chem. Int. Ed. 2001, 40, 4491-4493. 

14. Friestad, G. K.; Qin, J.  "Intermolecular Alkyl Radical Addition to Chiral N-Acylhydrazones Mediated by Manganese Carbonyl." J. Am. Chem. Soc. 2001, 123, 9922-9923.   [PDF]

13. Friestad, G. K.  "Addition of Carbon-Centered Radicals to Imines and Related Compounds" Tetrahedron 2001, 57, 5461-5496. 

12. Friestad, G. K.; Massari, S. E.  "Diastereoselective Vinyl Addition to Chiral Hydrazones via Tandem Thiyl Radical Addition and Silicon-Tethered Cyclization." Org. Lett. 2000, 2, 4237-4240.   [PDF]

11. Friestad, G. K.; Qin, J.  "Highly Stereoselective Intermolecular Radical Addition to Aldehyde Hydrazones from a Chiral 3-Amino-2-oxazolidinone." J. Am. Chem. Soc. 2000, 122, 8329-8330.   [PDF]

10. Kondru, R. K.; Beratan, D. N.; Friestad, G. K.; Smith, A. B., III; Wipf, P.  "Chiral Action at a Distance:  Remote Substituent Effects on the Optical Activity of Calyculins A and B."  Org. Lett. 2000, 2, 1509-1512. 

9. Friestad, G. K. "A Silicon Tether Approach for Diastereocontrol in Radical Addition to Chiral Hydrazones."  Org. Lett. 1999, 1, 1499-1501.   [PDF]

8. Smith, A. B., III; Friestad, G. K.; Barbosa, J., Bertounesque, E.; Duan, J. J.-W.; Hull, K. G.; Iwashima, M.; Qiu, Y.; Spoors, P. G.; Salvatore, B. A. "Total Synthesis of (+)-Calyculin A and (-)-Calyculin B:  Cyanotetraene Construction, Asymmetric Synthesis of the C(26-37) Oxazole, Fragment Assembly, and Final Elaboration."  J. Am. Chem. Soc. 1999, 121, 10478-10486. 

7. Smith, A. B., III; Friestad, G. K.; Barbosa, J., Bertounesque, E.; Hull, K. G.; Iwashima, M.; Qiu, Y.; Salvatore, B. A.; Spoors, P. G.; Duan, J. J.-W. "Total Synthesis of (+)-Calyculin A and (-)-Calyculin B: Asymmetric Synthesis of the C(9-25) Spiroketal Dipropionate Subunit."  J. Am. Chem. Soc. 1999, 121, 10468-10477. 

6. Grubb, L. M.; Dowdy, A. L.; Blanchette, H. S.; Friestad, G. K.; Branchaud, B. P. "An Approach to (+)-Pancratistatin from D-Glucose: A Conformational Lock Solves a Stereochemical Problem." Tetrahedron Lett. 1999, 40, 2691-2694. 

5. Smith, A. B., III; Cho, Y.; Friestad, G. K. "Convenient Wacker Oxidations with Substoichiometric Cupric Acetate." Tetrahedron Lett. 1998, 39, 8765-8768.

4. Smith, A. B., III; Friestad, G. K.; Duan, J. J.-W.; Barbosa, J.; Hull, K. G.; Iwashima, M.; Qiu, Y.; Spoors, P. G.; Bertounesque, E.; Salvatore, B. A.  "Total Synthesis of (+)-Calyculin A and (-)-Calyculin B." J. Org. Chem. 1998, 63, 7596-7597. 

3. Friestad, G. K.; Branchaud, B. P.  "A New Approach to the Pancratistatin C-Ring from D-Glucose:  Ferrier Rearrangement, Pseudoinversion and Pd-Catalyzed Cyclizations."  Tetrahedron Lett. 1997, 38, 5933-5936. 

2. Friestad, G. K.  Control of Reductive vs Non-Reductive Cyclization in Palladium-Catalyzed Aryl-Enone Conjugate Additions and Application to a Synthetic Approach to (+)-Pancratistatin.  Doctoral Dissertation, Department of Chemistry, University of Oregon, 1995.

1. Friestad, G. K.; Branchaud, B. P.  "Intramolecular Pd-Catalyzed Aryl-Enone Conjugate Additions.  Control of Reductive vs. Non-Reductive Cyclization."  Tetrahedron Lett. 1995, 36, 7047-7050.  
 

Other Publications

9. Friestad, G. K. "Practical Microwave Synthesis for Organic Chemists by C. Oliver Kappe, Doris Dallinger, and S. Shaun Murphree." J. Med. Chem. 2009, 52, 3596.  (invited book review)

8. G. K. Friestad "Dimanganese Decacarbonyl" in Electronic Encyclopedia of Reagents for Organic Synthesis; Paquette, L. A.; Fuchs, P.; Crich, D.; Molander, G., Eds.; Wiley: Chichester UK, in press.  (invited review)

7. Gregory K. Friestad "Ion-Radical Organic Chemistry: Principles and Applications, 2nd ed. by Zory Vlad Todres." J. Am. Chem. Soc. 2009, 131, 2418.  (invited book review)

6. Friestad, G. K. "Chloroiodomethane" in Electronic Encyclopedia of Reagents for Organic Synthesis; Paquette, L. A.; Fuchs, P.; Crich, D.; Molander, G., Eds.; Wiley: Chichester UK, http://www.mrw.interscience.wiley.com/eros/articles/rc110/frame.html, Article Online Posting Date: September 15, 2008.  (invited review)

5. Jiang, T.; Friestad, G. K. "Bis(ethoxythiocarbonyl)sulfide." in Electronic Encyclopedia of Reagents for Organic Synthesis; Paquette, L. A.; Fuchs, P.; Crich, D.; Molander, G., Eds.; Wiley: Chichester UK, www.mrw.interscience.wiley.com/eros/articles/rn00637/frame.html, Article Online Posting Date: April 15, 2006. (invited review)

4. Friestad, G. K.; Branchaud, B. P.  "Ammonium Tetrafluoroborate" in Encyclopedia of Reagents for Organic Synthesis; Paquette, L. A., Ed.; Wiley: New York, 1995; v. 1, pp. 199-200.  (invited review)

3. Friestad, G. K.; Branchaud, B. P.  "Cesium Fluoride" in Encyclopedia of Reagents for Organic Synthesis; Paquette, L. A., Ed.; Wiley: New York, 1995; v. 2, pp. 1042-1046.  (invited review)

2. Friestad, G. K.; Branchaud, B. P.  "Tetrafluoroboric Acid" in Encyclopedia of Reagents for Organic Synthesis; Paquette, L. A., Ed.; Wiley: New York, 1995; v. 7, pp. 4762-4765.  (invited review)

1. Branchaud, B. P.; Friestad, G. K.  "Vitamin B12" in Encyclopedia of Reagents for Organic Synthesis; Paquette, L. A., Ed.; Wiley: New York, 1995; v. 8, pp. 5511-5514.  (invited review)