Prof. Alfred Hassner

Prof.
Prof. Alfred Hassner
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CV

Education:  PhD Chemistry Univ of Nebraska (Cromwell);  Postdoctoral Harvard Univ (Fieser);

Research and Teaching:  Univ of Colorado Boulder Prof. of Chemistry 1957-1975;  SUNY Binghamton Leading Professor 1975-1984; Bar-Ilan Univ Professor Chemistry 1984-;

Visiting Prof:  Stanford U,  Weizmann Inst., U California  Berkeley, U California San Diego, U Maryland, U Wuerzburg, U Nijmegen, U Lyon, IIS Bangalore, U Tech Kyushu.

Honors. Humboldt Fellow, NCI Fellow, Lady Davis Fellow, A.W. Killam Award,  I.C.S. Prize for Excellence, Fulbright Senior Award,  Fellow Royal Soc. Chemistry, Past President Israel Chem Society,  Editorial board of  4 journals.

Invited lectures:  At universities and industrial laboratories (250).  Invited symposium or plenary lectures (44). Consultant to chemical, pharmaceutical companies.

Publications:  Over 315 Scientific publications (see selected Publications).  Editor: Small Ring Heterocycles (3 volumes);  Advances in Asymmetric Syntheses (3 vols); Synthesis of Heterocycles via Cycloadditions" (2 vols);

Books: Organic Syntheses Based on Name Reactions (1994, 2002, 2011) 

Research: Stereoselective introduction of N-functions (nitro, azido, isocyanate, nitrile oxide); synthesis of heterocycles (aziridines, azetines, azepines, pyridines);  introduced concept of regioselectivity; developed the use of 4-dialkylamino pyridines (DMAP) as superacylation catalysts; regioselective 2+2  ketene–olefin cycloadditions;  stereoselective intramolecular (3+2) dipolar cycloadditions (silyl nitronates, nitrile oxides, oximes); Michael Induced Ring Closures (MIRC) in synthesis of functionalized and enantiomerically pure cyclopentanes and in asymmetric synthesis of heterocycles via Ring Closing Metathesis ; ring enlargement (free radical); synthesis of potential anticancer and antiviral agents.

 

E-mail: hassna@mail.biu.ac.il  or hassna@biu.ac.il

 

Publications

Selected Publications (out of over 315)

 

  • A. Hassner and C.H. Heathcock, "Synthesis and Ring Opening of Fused Steroidal Aziridines", J. Org. Chem., 30, 1748 (1965).
  • A. Hassner and L.A. Levy, "Additions of Iodine Azide to Olefins. Stereospecific Introduction of Azide Functions", J. Am. Chem. Soc., 87, 4203 (1965).
  • A. Hassner, M.J. Haddadin and P. Catsoulacos, "Steroidal Indoxyls, Indoles and Quinolines", J. Org. Chem., 31, 1363 (1966).
  • F.W. Fowler, A. Hassner and L.A. Levy, "Stereospecific Introduction of Azide Functions into Organic Molecules", J. Am. Chem. Soc., 89, 2077 (1967).
  • A. Hassner and F.W. Fowler, "Synthesis and Reactions of 1-Azirines", J. Am. Chem. Soc., 90, 2869 (1968).
  • Hassner, "Regiospecificity. A Useful Terminology in Addition and Elimination Reactions", J. Org. Chem., 33, 2684 (1968).
  • Hassner, G.J. Matthews and F.W. Fowler, "The Reduction of b-Iodo Azides. A Stereospecific Synthesis of Aziridines", J. Am. Chem. Soc., 91, 5046 (1969).
  • Hassner, R.P.Hoblitt, C.H.Heathcock, J.E.Kropp, M.Lorber, "Electronic vs. Steric Effects in the Addition of INCO to Olefins", J. Am. Chem. Soc., 92, 1326 (1970).
  • Hassner, F. Boerwinkle and A.B. Levy, "Stereochemistry of Halogen Azide Additions to Olefins. The Stability of 3-Membered Ring Iodonium vs. Bromonium Ions", J. Am. Chem. Soc., 92, 4879 (1970).
  • Hassner, "Regiospecific and Stereospecific Introduction of Azide Functions into Organic Molecules", Accts. of Chem. Research, 4, 9 (1971).
  • Hassner, V.R. Fletcher and D.P.G. Hamon, "Stereoelectronic Effects in the Cycloaddition of Dichloroketene", J. Am. Chem. Soc., 93, 264 (1971).
  • A.B. Levy and A. Hassner, "Pyrolysis of Cyclopropyl Azides. A Route to 1-Azetines", J. Am. Chem. Soc., 93, 2051 (1971).
  • D.J. Anderson and A. Hassner, "Synthesis of Heterocycles via Cycloadditions to 1-Azirines", Synthesis, 483 (1975).
  • Hassner, R.H. Reuss and W.H. Pinnick, "Hydroxylation of Carbonyl Compounds via Silyl Enol Ethers", J. Org. Chem., 40, 3427 (1975).
  • Hassner and J.K. Rasmussen, "Recent Developments in the Synthetic and Mechanistic Uses of Chlorosulfonyl Isocyanate", Chem. Rev., 76, 389 (1976).
  • Hassner. R.M. Cory and N. Sartoris, "The Stereochemistry of Cycloadditions of Ketones to Unsymmetrical Alkenes; Evidence for Nonparallel Transitions States", J. Am. Chem. Soc., 98, 7698 (1976).     
  • Hassner and V. Alexanian, "Direct Room Temperature Esterification of Carboxylic Acids", Tet. Letts., 4475 (1978).
  • Hassner, P. Munger and B.A. Belinka, Jr., "A Novel Amination of Aromatic and Heteroatomatic Compounds", Tet. Letts. 23, 699 (1982).
  • Hassner, D. Birnbaum and L.M. Loew, "Charge-Shift Probes of Membrane Potential. Synthesis", J. Org. Chem., 49, 2546 (1984).
  • Hassner and K.S.K. Murthy, "Stereoselective Synthesis of Antitumor Agent Ptilocaulin and Its 7-Epimer", Tet. Letts, 27, 1407 (1986).
  • Hassner and A.,S. Amarasekara, "Phenylselenium Azide Addition to Alkenes. A New and Stereospecific Introduction of Se and N into Organic Molecules", Tet. Letts, 28, 5l85 (1987).
  • Hassner and R. Maurya, "A Route to Pyrrolizidines, Indolizidines and Quinolizidines Via Intramolecular Oxime Olefin Cycloadditions", Tetrahedron Lett., 30, 2289 (1989)
  • W. Dehaen, A. Hassner, "Stereoselectivity in Intramolecular 1,3-Dipolar Cycloadditions. Nitrile Oxides Versus Silyl Nitronates", Tetrahedron Lett., 31, 743 (1990).
  • Hassner, R. Maurya, A. Padwa and W.H. Bullock, "Thermally Induced Intramolecular Oxime Olefin Cycloadditions (IOOC) Leading to N-Bridged Systems. Stereochemis- try and Molecular Mechanics Calculations", J. Org. Chem., 56, 2775 (1991)
  • Hassner, "Stereochemical Effects During Synthesis of New Heterocycles via Intramolecular Dipolar Cycloadditions", in Heterocycles in Bio-organic Chemistry, J. Bergman, H.C. Van der Plas, M. Simonyi Eds, Royal Society of Chemistry, Cambridge, p. 130-143 (1991)
  • Hassner and B. Fischer, "New Chemistry of Oxazoles", Heterocycles, 36, 1441 (1993).
  • Hassner, R. Maurya, O. Friedman, H. E. Gottlieb, A. Padwa and D. Austin, "On the Conformation of Fused Five-Membered Heterocyclic Rings Derived from the Intramolecular Oxime Olefin Cycloaddition Reaction", J. Org. Chem., 58, 4539 (1993).
  • L. Zegelman, A. Hassner, Z. Mendel and E. Dunkelblum, "Synthesis and Field Bioassay of the Israeli Pine Bast Scale, Matsucoccus josephi, Female Sex Phermone", Tetrahedron Lett., 34, 355 (1993).
  • Hassner, S. Naidorf-Meir, H. E. Gottlieb and I. Goldberg, "Unusual Rearrangements in Cage Compounds due to Proximity Effects", J. Org. Chem., 58, 5699 (1993).
  • A.M. Belostotskii, H.E. Gottlieb and A. Hassner, “The Rate Determining Role of Strain for Nitrogen Inversion in Polycyclic Tertiary Amines”, J. Am. Chem. Soc., 118, 7783 (1996).
  • T. Yechezkel, E. Ghera, N.G. Ramesh and A. Hassner, “Asymmetric Synthesis of Substituted Cyclopentanes via Michael-Initiated Ring Closure Reactions”, Tetrahedron Asymm. 7, 2423 (1996).
  • I.N.N. Namboothiri, A. Hassner and H.E. Gottlieb, “A Highly Stereoselective One-Pot Tandem Consecutive 1,4-Addition Intramolecular 1,3-Dipolar Cycloaddition Strategy for the Construction of Functionalized Five- and Six-Membered Carbocycles”, J. Org. Chem., 62, 485 (1997).
  • Hassner, V. Kleiman and E. Ghera, “Remote Asymmetric Inductions in Michael Additions of Allyl Sulfones”, J. Org. Chem. 64, 8 (1999).
  • E. Falb, Y. Bechor, A. Nudelman, A. Hassner, A. Albeck, and H.E. Gottlieb “IOOC Route to Substituted Chiral Pyrrolidines. Potential Glycosidase Inhibitors" J. Org. Chem. 64, 498 (1999).
  • R. Kumeraswaran, T. Balasubramian and A. Hassner, “Synthesis of Enantiopure Pyrrolidine and Piperidine Derivatives via Ring Closing Metathesis” Tetrahedron Lett., 41, 8157 (2000).
  • Hassner, E. Ghera, T. Yechezkel, V. Kleiman, T. Balasubramian and D. Ostercamp, “Stereoselective and Enantioselective Synthesis and 5-membered Rings via Conjugate Additions of Allylsulfone Carbanions”. Pure and Applied Chem. 72, 1671 (2000).
  • A.M. Belostotskii, H. Keren-Yeshuah, J. Lexner, and A. Hassner, “New 3¢-Deoxythymidines Bearing Nucleophilic 3¢-Substituents”, Nucleosides, Nucleotides and Nucleic Acids, 20, 93-101 (2001).
  • I.N.N. Namboothiri and A. Hassner, “Stereoselective Intramolecular 1,3-Dipolar Cycloadditions”, Topics of Current Chemistry 216, 1-49 (2001)
  • Ch. Zhou and A. Hassner, "Synthesis and Anticancer Activity of Novel Chiral D-Glucose Derived Bis-imidazoles and Their Analogs", Carbohydrate Research 333, 313-326 (2001).
  • R. Kumareswaran and A. Hassner, "Asymmetric Synthesis and N-Acetyl-(R)-Coniine and N-Boc-(2R, 6R)-Solenopsin A via Ring-Closing Metathesis", Tetrahedron: Asymm. 12, 2269-2276 (2001).
  • T. K. Pradhan and A. Hassner, "A Facile Synthesis of (n+3) and (n+4) Ring Enlarged Lactones as well as of Spiro Keto Lactones from n-Membered Cycloalkanones", Synthesis, 3361-3371 (2007).
  • Hassner, D. Yagudayev, T.K. Pradhan, A. Nudelman and B. Amit, "Light-Sensitive Protecting Groups for Amines and Alcohols. The Photosolvolysis of N-Substituted 7-Nitroindolines", Synlett 2405-2409 (2007).
  • A M. Belostotskii, E. Genizi, and A. Hassner, "Essential Reactive Intermediates in  Nucleoside Chemistry: Cyclonucleoside Cations" Organic and Biomolecular Chemistry  10, 6624-6628 (2012).

  • A. Hassner, S. C. R Bandi, R. Panchgalle, "A Mild and Efficient Room Temperature Protection of Ketones or Aldehydes as 1,3-Dioxolanes Under Neutral Conditions",  Synlett  2773 (2012).

  • A. Hassner, S. C. R. Bandi, "High Yield and Rapid C-C Bond Formation from Alcohols. Allylation by Means of TiCl4", Synlett, in press, (2013).

 

Research

Organic Chemistry, Stereochemistry, Medicinal Chemistry, Heterocyclic

1. Cycloadditions

2. New Synthetic Methods