PausonKhand-type reaction mediated by Rh(I) catalysts*
Nakcheol Jeong, Byung Ki Sung, Jin Sung Kim, Soon Bong Park, Sung Deok
Seo, Jin Young Shin, Kyu Yeol In, and Yoon Kyung Choi
Department of Chemistry and Division of Chemistry and
Molecular Engineering, Korea University, Seoul, 136-701, Korea
Abstract: Cocyclization of alkynes, alkenes, and carbon monoxide
by transition metals (known as PausonKhand reaction when dicobalt
octacarbonyl complexes are used) has been accepted as one of the most
powerful tools in the synthesis of cyclopentenones. Despite significant
progress in the various aspects of the reaction, we still needed new
catalysts to expand the scope of the reaction further.
We found rhodium (I) catalysts, e.g., RhCl(PPh3)3, trans-RhCl(CO)(PPh3)2,
RhCl-(CO)(dppe), and trans-[RhCl(CO)(dppp)]2, were also effective for
this transformation. The scope and the efficiencies of the reaction
could be tuned and expanded by the choice of catalysts. For example,
we were able to devise an enantioselective PK-type reaction and a tandem
strategy employing two catalysts in one pot. These results will be presented.
*Lecture presented at the 11th IUPAC International
Symposium on Organometallic Chemistry Directed Towards Organic Synthesis
(OMCOS-11), Taipei, Taiwan, 22-26 July 2001. Other presentations are
presented in this issue, pp.1-186.
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