Diastereoselective three-component synthesis of beta-amino carbonyl compounds using diazo compounds, boranes, and acyl imines under catalyst-free conditions
Schaus, Scott E.
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Citation (published version)Yi Luan, Jie Yu, Xiaowei Zhang, Scott E Schaus, Ge Wang. 2014. "Diastereoselective Three-Component Synthesis of beta-Amino Carbonyl Compounds Using Diazo Compounds, Boranes, and Acyl Imines under Catalyst-Free Conditions." JOURNAL OF ORGANIC CHEMISTRY, Volume 79, Issue 10, pp. 4694 - 4698 (5). https://doi.org/10.1021/jo5003505
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.
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