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Diastereoselective three-component synthesis of ?-amino carbonyl compounds using diazo compounds, boranes, and acyl imines under catalyst-free conditions.

ABSTRACT: Diazo compounds, boranes, and acyl imines undergo a three-component Mannich condensation reaction under catalyst-free conditions to give the anti ?-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 ?-amino carbonyl compounds are valuable intermediates, which can be transformed to many potential bioactive molecules.

SUBMITTER: Luan Y

PROVIDER: S-EPMC4033649 | biostudies-literature | 2014 May

REPOSITORIES: biostudies-literature

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Diastereoselective three-component synthesis of β-amino carbonyl compounds using diazo compounds, boranes, and acyl imines under catalyst-free conditions.

Luan Yi Y Yu Jie J Zhang Xiaowei X Schaus Scott E SE Wang Ge G

The Journal of organic chemistry 20140507 10

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. ...[more]

PMID: 24787904

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