Diastereoselective three-component synthesis of β-amino carbonyl compounds using diazo compounds, boranes, and acyl imines under catalyst-free conditions.
Diazo compounds, boranes, and acyl imines undergo a three-component Mannich condensation reaction under catalyst-free conditions to give the anti β-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 β-amino carbonyl compounds are valuable intermediates, which can be transformed to many potential bioactive molecules.
School of Materials Science and Engineering, University of Science and Technology Beijing , 30 Xueyuan Road, Haidian District, Beijing 100083, P. R. China.
Yi
Y
Luan
Jie
J
Yu
Xiaowei
X
Zhang
Scott E
SE
Schaus
Ge
G
Wang
D000596:Amino Acids / Q000138:chemical synthesis* / Q000737:chemistry; D001391:Azo Compounds / Q000737:chemistry*; D001880:Boranes / Q000737:chemistry*; D002384:Catalysis; D007097:Imines / Q000737:chemistry*; D015394:Molecular Structure; D013237:Stereoisomerism
D000596:Amino Acids; D001391:Azo Compounds; D001880:Boranes; D007097:Imines