Diastereoselective Three-Component Synthesis of β-Amino Carbonyl Compounds Using Diazo Compounds, Boranes, and Acyl Imines under Catalyst-Free Conditions

作者：Luan, Yi; Yu, Jie; Zhang, Xiaowei; Schaus, Scott E.; Wang, Ge^*

来源：Journal of Organic Chemistry, 2014, 79(10): 4694-4698.

DOI：10.1021/jo5003505

• ALPHA-DIAZOCARBONYL COMPOUNDS
• ETHYL DIAZOACETATE
• ENANTIOSELECTIVE ADDITION
• ASYMMETRIC ALLYLBORATION
• MULTICOMPONENT REACTIONS
• CF3-SUBSTITUTED BORANES
• REGIOSPECIFIC SYNTHESIS
• BORONIC ACIDS
• ESTERS
• TRIALKYLBORANES

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.

• 出版日期2014-5-16
• 单位北京科技大学