High Selectivity Induced by Neighbouring-Group Effects in C-C Bond-Forming Reactions with Organotransition Metal Reagents
- 1 July 1995
- journal article
- review article
- Published by Georg Thieme Verlag KG in Synthesis
- Vol. 1995 (07) , 745-755
- https://doi.org/10.1055/s-1995-4010
Abstract
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.Keywords
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