Multicomponent Mannich Reactions Using Boron Enolates Derived from Diazo Esters and 9-BBN

摘要

Diazo esters, arylboranes and carbamoyl imines undergo a 3-component Mannich condensation reaction. Catalyzed by Cu(II) salts, the reaction affords the corresponding isocyanate Mannich product; one that can be easily trapped in situ by other nucleophiles. The Mannich condensation corresponds to an α,α-disubstituted enolate addition to imines. The reaction was rendered asymmetric using the (-)-phenylmenthol ester in good yield and selectivities.