Lithium diisopropylamide: solution kinetics and implications for organic synthesis.
Lithium diisopropylamide (LDA) is a prominent reagent used in organic synthesis. In this Review, rate studies of LDA-mediated reactions are placed in the broader context of organic synthesis in three distinct segments. The first section provides a tutorial on solution kinetics, emphasizing the characteristic rate behavior caused by dominant solvation and aggregation effects. The second section summarizes substrate- and solvent-dependent mechanisms that reveal basic principles of solvation and aggregation. The final section suggests how an understanding of mechanism might be combined with empirical methods to optimize yields, rates, and selectivities of organolithium reactions and applied to organic synthesis.
Collum
David B
DB
Department of Chemistry and Chemical Biology, Baker Laboratory, Cornell University, Ithaca, NY 14853-1301, USA. dbc6@cornell.edu
McNeil
Anne J
AJ
Ramirez
Antonio
A
D019281:Dimerization; D007700:Kinetics; D008024:Ligands; D011437:Propylamines / Q000737:chemistry*; D012997:Solvents; D013329:Structure-Activity Relationship
D008024:Ligands; D011437:Propylamines; D012997:Solvents; C007442:diisopropylamine