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honoring

Professor K. Barry Sharpless
The Scripps Research Institute
The Sharpless Lab Web Site

March 10, 2006

Crowne Plaza Hotel
White Plains, NY
(Directions)

[ photos ]

Abstract:
Despite of the high energy content, organic azides and alkynes are chemically orthogonal to an unusually broad range of reagents, solvents, and other functional groups. Although their thermal cycloaddition reaction is exceedingly slow due to the high energy of activation (ca. 24-26 kcal/mol), their reactivity towards each other can be revealed by means of an appropriate catalyst. For example, copper(I) results in the formation of the 1,4-disubstituted 1,2,3-triazoles, while ruthenium(II) catalyzes formation of the complementary 1,5-regioisomers. Catalytic azide-alkyne cycloadditions are now among the most efficient ways to permanently unite diverse structures by means of the triazole connections -- permanent chemically inert links that bring together blocks with desired functionality.

Representative examples from our laboratories, as well as important mechanistic aspects of these processes and their implications for the design of other catalytic systems will be discussed in the lecture

Abstract:
I have borrowed my title from Leo Tolstoy’s famous short story How Much Land Does a Man Need? The original is a morality tale writ large, a short story about a man who, in his lust for land, forfeits everything, including his own life. However, though I read it some 50 years ago, it has stuck as a vivid memory and a meaningful icon.

My lecture will consider the chemists’ love affair with reactivity. How much more ‘new reactivity’ we think we need, and how by seeing the known in new light we might find creating new properties and functions much easier than we had ever imagined possible, and how chemical orthogonality can enable us to create “Trojan Horse” molecules using Nature’s own biochemical tools without Her ever noticing.

Biography:
W.M. Keck Professor of Chemistry
The Scripps Research Institute, La Jolla, CA 92037

K. Barry Sharpless has always been exclusively interested in useful chemistry. Since he regards the oxidation of olefins as the single most versatile, powerful and reliable class of transformations in organic synthesis, Sharpless concentrates on expanding the scope of existing oxidative reactions and discovering new ones.

Sharpless is best known for discovering three “name” reactions, general methods for catalytic asymmetric epoxidation, dihydroxylation, and aminohydroxylation. His Nobel Prize citation says, “many scientists have identified Sharpless’s epoxidation [discovered in 1980 with Tsutomu Katsuki] as the most important discovery in the field of synthesis during the past few decades.”

Descended from one of the original land purchasers in William Penn’s New World venture, Barry Sharpless received a Quaker education at the Friends Central School, Haverford, Pennsylvania. In 1963 he graduated from Dartmouth College, where he was introduced, most fortuitously, to the wonders of chemistry and chemical research by T. A. Spencer. Following graduate research with E. E. vanTamelen at Stanford University, Sharpless completed postdoctoral studies with J. P. Collman, also at Stanford, and at Harvard University with Konrad Bloch. While Sharpless was a graduate student, he recognized a role model in D. H. R. Barton; later, and until his death, Sir Derek became Sharpless’s valued mentor.

Sharpless set up his own laboratory when in 1970 he became an assistant professor at the Massachusetts Institute of Technology. Except for several years in the 1970s when he was a member of Stanford’s chemistry faculty, Sharpless remained at MIT until moving to the Scripps Research Institute (TSRI) in 1990. At TSRI he is W. M. Keck Professor of Chemistry and a member of the Skaggs Institute for Chemical Biology.

Sharpless continues at TSRI his career-long search for useful new reactivity and general methods for selectively controlling chemical reactions. A recent creation is click chemistry, a set of powerful, virtually 100% reliable, selective reactions for the rapid synthesis of new compounds via heteroatom links. Click chemistry is integral now to all research within the Sharpless Lab, including numerous collaborations with biologists both within TSRI and beyond its walls.