Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 12, Issue 1, Pages 30-37Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.200500782
Keywords
allylation; asymmetric synthesis; chirality; hydrosilylation; silicon
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The exploitation of the asymmetry at silicon in stereoselective synthesis is an exceptionally challenging task. Initially, silicon-stereogenic silanes have been utilized to elucidate the stereochemical course of substitution reactions at silicon. Apart from these mechanistic investigations, only a handful of synthetic applications with an asymmetrically substituted silicon as the stereochemical controller have been reported to date. In these transformations the chiral silicon functions as a chiral auxiliary. Conversely, a direct transfer of chirality from silicon to carbon during bond formation and cleavage at silicon has remained open until its recent realization in both inter- and intramolecular reactions. In this Concept, the pivotal considerations in relation to the nature of suitable silanes as well as mechanistic prerequisites for an efficient chirality transfer will be discussed.
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