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Hetero‐Aggregate Compounds of Aryl and Alkyl Lithium Reagents: A Structurally Intriguing Aspect of Organolithium Chemistry
Author(s) -
Gossage Robert A.,
Jastrzebski Johann T. B. H.,
van Koten Gerard
Publication year - 2005
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.200462103
Subject(s) - aryl , alkyl , organolithium compounds , lithium (medication) , reagent , chemistry , aggregate (composite) , organic chemistry , materials science , nanotechnology , ion , biology , deprotonation , endocrinology
Abstract Organolithium compounds are often depicted as mononuclear species. However, such compounds are in fact aggregated species and can form hetero‐aggregates containing different organic groups, including heteroatom groups. In reactions involving organolithium reagents, the “pure” homo‐aggregate organolithium compound can change into a hetero‐aggregate, which has a different structure and reactivity to the homo‐aggregate. This fact is often overlooked. When there are chiral centers in the organolithium reagent or the substrate, diastereoselective self‐assembly (the preferential formation of a particular diastereoisomeric aggregate) plays a role. The importance of these contributions in understanding the structure and reactivity patterns of organolithium reagents is the focus of this Minireview.