Sharpless, Barry

Excerpt 4F is taken from an article written by Demko and Sharpless. (Barry Sharpless was a co-recipient of the Nobel Prize in Chemistry in 2001 for his work on chirally catalyzed oxidation reactions.) In this article, the authors propose a way to synthesize aromatic tetrazoles from nitriles in water, using only sodium azide and a zinc salt. Water, despite its obvious advantages (i.e., safe and inexpensive), rarely succeeds as a solvent in organic synthesis. Thus, a synthesis that uses water successfully is an important scientific accomplishment. 

For developing osmium catalyzed oxidation methods for preparing chiral com pounds of high optical pu rity Professor K Barry Sharpless (Scripps Research Institute) shared the 2001 Nobel Prize in chemistry... 

Sesquiterpenoid. 203, 1071 Sex hormone, 1082-1083 Sharpless, K. Barry. 734 Sharpless epoxidation, 735 Shell (electron), 5 capacity of, 5 Shielding (NMR). 442 Si prochirality, 315-316 Sialic acid. 997 Side chain (amino acid), 1020 Sigma (cr) bond, 11 symmetry of, 11 Sigmatropic rearrangement, 1191-1195... 

A different approach to making chiral drugs is asymmetric synthesis. An optically inactive precursor is converted to the drug by a reaction that uses a special catalyst, usually an enzyme (Chapter 11). If all goes well, the product is a single enantiomer with the desired physiological effect In 2001, William S. Knowles, Ryogi Noyori, and K. Barry Sharpless won the Nobel Prize in chemistry for work in this area. 

For a related complex, see W. V. Konze, B. L. Scott, and G. J. Kubas, J. Am. Chem. Soc. 124 (2002), 12 550 Bill Knowles shared the 2001 Nobel Prize (with Barry Sharpless and Ryoji Noyori) for his development of catalytic asymmetric hydrogenation. 

K. BARRY SHARPLESS, Scripps Institute, La Jolla, California, USA... 

The asymmetric dihydroxylation protocol was the second massive contribution by Professor Barry Sharpless to synthetic organic chemistry. The first procedure, introduced with Katsuki, involves the catalytic asymmetric epoxida-tion of allylic alcohols. A typical example is shown in Scheme 17, wherein ( )-allylic alcohol (23) is epoxidized with tert-b utyl hyd roperox ide, in the presence of titanium tetra-isopropoxide and optically active diethyl tartrate to give the... 

The full paper on titanium-catalysed asymmetric epoxidation appeared in 1987 [6], once the improved catalytic procedure in the presence of molecular sieves had already been fully developed [5]. On the other hand, excellent "autobiographic" accounts have also been published in which "Everything You Ever Wanted to Know About the Discovery of Asymmetric Epoxidation" is honestly and vividly exposed by K. Barry Sharpless [4] [7]. 

I. Noyori, R. Ohta, M. Hsiao, Y. Kitamura, Ma. Ohta, T. Takaya, H. J. Am. Chem. Soc. 1986, 108, 7117. Ryoji Noyori (Japan, 1938—) and Herbert William S. Knowles (USA, 1917—) shared half of the Nobel Prize in Chemistry in 2001 for their work on chirally catalyzed hydrogenation reactions. K. Barry Sharpless (USA, 1941—) shared the other half for his work on chirally catalyzed oxidation reactions. 

K. Barry Sharpless United States chirally catalyzed oxidation reactions... 

The enantioselective oxygenation procedures, epoxidation and dihydroxylation, developed by Barry Sharpless have dominated single-enantiomer organic synthesis. Recently, several additional methods for enantioselective oxidation have been developed, based on the a-functionalization of carbonyl compounds. 

Submitted by Paul G. Gassman and Thomas L. Guggenheim. Checked by Curtis E. Adams and K. Barry Sharpless. 

Checked by Ronaldo A. Pilli, Kenneth S. Kirshenbaum, Clayton H. Heathcock, and K. Barry Sharpless. 

Submitted by Todd K. Jones and Scott E. Denmark.1 Checked by Steven M. Viti and K. Barry Sharpless. 

Submitted by Dale L. Boger and Michael D. Mullican. Checked by Drew B. Burns and K. Barry Sharpless. 

Professor K. Barry Sharpless, Nobel Laureate for Chemistry (2001), has provided an elegant description that captures the integral role of mass spectrometry leading to success with in situ Click chemistry, and this sentiment is similarly valid for in situ DCC ... 

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