Multicomponent Mannich reactions with boron enolates derived from diazo esters and 9-BBN.

ABSTRACT: 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 by using the (-)-phenylmenthol ester in good yield and selectivities.

SUBMITTER: Luan Y 

PROVIDER: S-EPMC4671502 | biostudies-literature | 2011 May

REPOSITORIES: biostudies-literature