Professor

B.A. (1963), Albright College
Ph.D. (1967) Princeton University
Postdoctoral Fellow ('67-69) Ohio State University

J.D. (1978) Temple University

OFFICE
Beury Hall 448

MAILING ADDRESS
Department of Chemistry
Beury Hall 130
1901 N. 13th Street
Philadelphia, PA 19122

PHONE
office: 215-204-7154
fax: 215-204-1532
lab: 215-204-3456

E-MAIL
grkrow@temple.edu

RESEARCH GROUP

Organic

Research Interests

Synthetic and Mechanistic Organic Chemistry

Small Bridged-Ring Nitrogen Heterocycles.   Synthetic methods are under development to prepare methanopyrrolidines (2-azabicyclo[2.1.1]hexanes) 1 with heteroatom, alkyl, aryl, or acyl functionality at the various ring positions C 1 -C 6 .   Our major current efforts are directed toward discovery of efficient photochemical or rearrangement routes that will allow for stereocontrol and regiocontrol in the introduction of substituents.

Bioactive Molecule Synthesis.   We are applying insights obtained from the preparation of methanopyrrolidines 1 to the generation of monomer pools for incorporation into ß-peptide tertiary amide foldamers 2 .   Other projects involve synthesis of conformationally constrained analogs of heteroatom-functionalized methanoprolines 3 in the search for more stable forms of collagen.

Selected Publications

K.L. Gorres, R. Edupuganti, G.R. Krow, "Conformational preferences of substances for human prolyl 4-hydroxylase." Biochemistry. (2008) , 47, 36, 9447-9455.

G.R. Krow, P.E. Sonnet, "Carbamate-stabilized anions of 2-azabicyclo[2.1.1]hexanes." Tetrahedron. (2008) , 64, 30-31, 7131-7135.

G.R. Krow, D. Gandla, W.W. Guo, "Neighboring group participation in the additions of iodonium and bromonium ions to N-alkoxycarbonyl-2-azabicyclo[2.2.n]alk-5-enes (n=1,2)." Journal of Organic Chemistry. (2008) , 73, 6, 2114-2121.

G.R. Krow, D. Gandla, W.W. Guo, "Selectfluor as a nucleofuge in the reactions of azabicyclo[n.2.1]alkane beta-halocarbamic acid esters (n=2,3)." Journal of Organic Chemistry. (2008) , 73, 6, 2122-2129.

G.R. Krow, Q.L. Huang, S.W. Szczepanski, F.H. Hausheer, and P.J. Carroll, "Stereoselectivity in Diels-Alder reactions of diene-substituted N-alkoxycarbonyl-1,2-dihydropyridines." Journal of Organic Chemistry. (2007) , 72, 3458-3466.

G.R. Krow, Q.L. Huang, and G.L. Lin, "5-carboxy-2-azabicyclo [2.1.1] hexanes as precursors of 5-halo, amino, phenyl, and 2-methoxycarbonylethyl methanopyrrolidines." Journal of Organic Chemistry. (2006) , 71, 2090-2098.

G. R. Krow, G. Lin, and F. Yu, "The Rearrangement Route to 3-Carboxy- and 3-Hydroxymethyl-2-azabicyclo[2.1.1]hexanes: 3,5-Methanoprolines." Journal of Organic Chemistry. (2005) , 70 , 590-595.

C. L. Jenkins, G. Lin, J. Duo, D. Rapolu, I. A. Guzei, R. T. Raines, G. R. Krow, "Substituted 2-Azabicyclo[2.1.1]hexanes as Constrained Proline Analogues:   Implications for Collagen Stability," Journal of Organic Chemistry . (2004) , 69 , 8565.

G. R. Krow, G. Lin, K. Moore, A. M. Thomas, C. DeBrosse, C. W. Ross, III,   and H. G. Ramjit, "Novel Selectfluor and Deoxo-Fluor   Mediated Rearrangements.   New 5(6)-Methyl and Phenyl Methanopyrrolidine Alcohols and Fluorides."   Organic Letters (2004) , 6 , 1669-72.

G. R. Krow and K. C. Cannon, "2-Azabicyclo[2.2.0]hex-5-enes and 2-Azabicyclo[2.2.0]hexanes. A Review." Heterocycles , (2004) , 64 , 577-604.

G. R. Krow and K. C. Cannon, "Azabicyclo[2.1.1]hexanes. A Review." Heterocycles , (2004) , 62 , 877-898.