Hetero-aggregate compounds of aryl and alkyl lithium reagents: a structurally intriguing aspect of organolithium chemistry.
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.
Gossage
Robert A
RA
Chester Woodleigh Small Laboratory of Organic Chemistry, Department of Chemistry, Acadia University, Wolfville, Nova Scotia B4P 2R6, Canada. r.gossage@acadiau.ca
Jastrzebski
Johann T B H
JT
van Koten
Gerard
G