High Selectivity Induced by Neighbouring-Group Effects in C-C Bond-Forming Reactions with Organotransition Metal Reagents

Thomas Kaufmann

doi:10.1055/s-1995-4010

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

Abstract

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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

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