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Angewandte
Obituary
Ivar K. Ugi (1930–2005): Multicomponent Reactions, Computer
and Phosphorus Chemistry
Ivar Ugi, Professor of Organic Chemistry at the Technische Universitt Mnchen, died on September 29, 2005,
shortly after his 75th
birthday, after a long
and serious illness.
Ugi was born in
Kurressaare on the
Estonian island of
Saaremaa. His family
moved to Germany in
1941 as a result of the
Molotov–Ribbentrop
Pact. After his Abitur,
he initially studied
chemistry and mathematics at Tbingen
(1949–1952) but later concentrated
solely on chemistry. Nevertheless, his
love for mathematics remained influential during his subsequent scientific
career. In 1952 he moved to the
Ludwig-Maximilians-Universitt Mnchen, where he obtained his PhD
(1954) and habilitation (1959) with
Rolf Huisgen. After a number of years
at Bayer A.G. (1962–1968), he followed
the calling for independent university
research and joined the University of
Southern California, Los Angeles, as
professor. He returned to Germany in
1971, when he was appointed successor
to Friedrich Weygand at the Technische
Universitt Mnchen.
The proof of the existence of pentazole was an initial “explosive” preparative result.[1] During the course of his
habilitation, he discovered the fourcomponent condensation (4-CC) reaction in which a carbonyl compound, an
amine, an isonitrile, and a carboxylic
acid react in a unique manner to form
(in the widest possible sense) a tripeptide.[2] This reaction, later known as the
Ugi reaction, proved to be extremely
fruitful and successful. The chemistry of
the required isonitriles was still relatively undeveloped, but this was now
rapidly rectified.[3] The possibility of
generating new chirality in 4-CC reactions led to preparative work on chiral
ferrocene derivatives and to group
theory considerations on the phenomenon of chirality.[4]
Angew. Chem. Int. Ed. 2006, 45, 193
Chemie
Ugi realized quite early on that the
4-CC reaction, being a multicomponent
reaction, paved a way to an unimagined
diversity of products with the aid of
combinatorial methods.[5] He calculated
that a batch of forty of each representative of the individual components would
lead to an ensemble of 2 560 000 compounds. Since that time, combinatorial
chemistry has evolved to become a
leading paradigm in drug discovery.
Ivar Ugi was enthused by the
abstract algebraic model of chemistry,
developed in collaboration with the
mathematician Jim Dugundji,[6] in
which assemblies of molecules were
represented by matrices of bonds and
free electrons, and reactions were rep[ ]
resented as their difference (
* ).
The generation of previously unknown
reactions by nonempirical selection
rules fascinated him considerably.
Group theory considerations on stereochemistry led inter alia to the postulatation of an alternative mechanism to
the established “Berry pseudorotation”
for the rearrangement of ligands of
pentacoordinated phosphorus compounds, namely, the “turnstile rotation”.[7] The discussion that ensued had
the input of heart and soul that was
typical of Ugi and resulted in much
theoretical and preparative work on
phosphorylation reactions and the necessary protecting groups.
The strength of will with which he
recovered his speech after a stroke in
1992 left a deep impression on all those
close to him. From then onwards, he
devoted himself totally to multicomponent reactions and their potential in
combinatorial chemistry.
Ugi was honored many times. In
1987, he became a member of the Royal
Swedish Academy of Sciences, and, in
1991, he was appointed member of the
Academy of Sciences of his country of
birth, Estonia. He was awarded the Emil
Fischer and Max Bergmann medals, and
he received the Philip Morris Prize for
his work on the algebraic model of
chemistry. Several companies devoted
to the application of multicomponent
chemistry were founded by former
members of his group.
Whoever allowed themselves to be
infected by the enthusiasm of the academic teacher Ivar Ugi could find farreaching and enduring inspiration in his
presence.
“Ivar Ugi does not swim against the
current, that we would not allow. But he
certainly swims athwart the current”, one
eulogist said on the occasion of his 60th
birthday. The sole description of his
scientific passion and success portrays
Ivar Ugi inadequately. He will also be
remembered by his enjoyment of social
intercourse, of discussion, of controversial argument, and by his passion to
narrate. His stories about Josef Bem, his
ancestor and a fighter on many fronts,
are unforgettable to those of us who
worked with him. His talent to entertain
guests and his enthusiasm to place high
expectations on young chemists are
legendary.
With Ivar Ugi, the scientific community has lost a creative visionary of
chemistry.
Peter Lemmen, Eric Fontain, Johannes Bauer
Technische Universitt Mnchen
[1] R. Huisgen, I. Ugi, Chem. Ber. 1957, 90,
2914.
[2] I. Ugi, R. Meyr, U. Fetzer, C. Steinbrckner, Angew. Chem. 1959, 71, 386.
[3] I. Ugi, Isonitrile Chemistry, Academic
Press, New York, 1971.
[4] E. Ruch, I. Ugi, Theoret. Chim. Acta
(Berl.) 1966, 4, 287.
[5] A. DHmling, I. Ugi, Angew. Chem. 2000,
112, 3300; Angew. Chem. Int Ed. 2000, 39,
3168.
[6] J. Dugundji, I. Ugi, Top. Curr. Chem.
1973, 39, 19.
[7] I. Ugi, D. Marquarding, H. Klusacek, P.
Gillespie, F. Ramirez, Accounts Chem.
Res. 1971, 4, 288.
DOI: 10.1002/anie.200503978
[*] Photo: Reporter PR GmbH, Frankfurt.
2006 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
193
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