Selective transformations mediated by main-group organometallics*
Paul Knochel**, Andreas Boudier, Lars O. Bromm, Eike Hupe,
Jesús A. Varela, Alain Rodriguez, Christopher Koradin, Tanasri
Bunlaksananusorn, Hamid Laaziri, and Frédéric Lhermitte
Department of Chemistry, Ludwig-Maximilians-University,
Butenandtstrasse 5-13, D-81377 Munich, Germany
Abstract: Main-group organometallics are useful intermediates
for the chemoselective and diastereoselective C-C bond formation. The
boron-zinc exchange is a unique way for preparing chiral secondary alkylzinc
reagents which are configurationally stable over a wide temperature
scale. Coupled with the thermal rearrangement of tertiary organoboranes,
a broad range of open-chain and cyclic polyfunctional molecules have
been prepared. In addition, several examples of a diastereoselective
remote C-H activation have been studied. The second part shows that
the main-group metallic alkoxides such as t-BuOK can be used for the
performance of catalytic reactions such as a new indole synthesis.
*Lecture presented at the 13th International
Conference on Organic Synthesis (ICOS-13), Warsaw, Poland, 1-5 July
2000.
** Corresponding author
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