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Pure Appl. Chem., 2000, Vol. 72, No. 9, pp. 1699-1703

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.