Multicomponent Mannich Reactions with Boron Enolates Derived from Diazo Esters and 9-BBN
作者:Yi Luan、Scott E. Schaus
DOI:10.1021/ol200766t
日期:2011.5.6
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.
Diastereoselective Three-Component Synthesis of β-Amino Carbonyl Compounds Using Diazo Compounds, Boranes, and Acyl Imines under Catalyst-Free Conditions
作者:Yi Luan、Jie Yu、Xiaowei Zhang、Scott E. Schaus、Ge Wang
DOI:10.1021/jo5003505
日期:2014.5.16
Diazo compounds, boranes, and acyl imines undergo a three-component Mannich condensation reaction under catalyst-free conditions to give the anti beta-amino carbonyl compounds in high diastereoselectivity. The reaction tolerates a variety of functional groups, and an asymmetric variant was achieved using the (-)-phenylmenthol as chiral auxiliary in good yield and selectivity. These beta-amino carbonyl compounds are valuable intermediates, which can be transformed to many potential bioactive molecules.