Structure of reactive aggregate of lithium reagents and its application to the generation of highly-activated reagents.

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Organolithiums are one of the most frequently-used reagents in synthetic chemistry. To better understand their reactivity and reaction mechanisms, it is necessary to elucidate the structure of reactive organolithium reagents. We found that a ternary complex reagent of lithium ester enolate-chiral diether-lithium diisopropylamide was formed in an equimolar mixture of these reagents in toluene based on low-temperature NMR spectroscopy. This complex shows high reactivity and enantioselectivity in an asymmetric Michael reaction.