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Synthesis 1995; 1995(7): 745-755
DOI: 10.1055/s-1995-4010
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High Selectivity Induced by Neighbouring-Group Effects in C-C Bond-Forming Reactions with Organotransition Metal Reagents

Thomas Kaufmann*
  • *Organisch-Chemisches Institut der Universität Münster, Corrensstr. 40, D-48149 Münster, Germany, Fax +49(251)839772
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Publication Date:
31 December 2000 (online)

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Basic groups (e.g. OH, OMe, NMe2) in the neighbourhood of electrophilic functional groups of organic molecules are recognized by nucleophilic organotransition reagents [e.g. MeCrCl2(THF)3, Bu2Mn, (allyl)2VCl, NCCH2FeCl, EtO2CCH2CoCl, [vinylTi(OiPr)4]Li] and accelerate or inhibit C-C bond-forming reactions at the electrophilic function. These neighbouring-group effects enable highly selective (chele- and anticheleselectivity, stereoselectivity) reactions on ketones, aldehydes, epoxides and vinyl bromides.

selective C-C bond formation - neighbouring-group effects - chele- and anticheleselectivity - stereoselectivity - transition metal reagents