期刊
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
卷 136, 期 50, 页码 17669-17673出版社
AMER CHEMICAL SOC
DOI: 10.1021/ja510963k
关键词
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资金
- NSERC
- OGS
The use of alpha-boryl enamine and enamide linchpins in the synthesis of nitrogen heterocycles has been demonstrated. Boryl enamines provide ready access to the corresponding alpha-halo aldehydes, which undergo regioselective annulation to form borylated thiazoles. A condensation/amidation sequence converts alpha-boryl aldehydes into stable alpha-boryl enamides without concomitant C -> N migration. We also show that palladium-catalyzed cyclization of alpha-boryl enamides leads to synthetically versatile isoindolones. These molecules can be subsequently used to access polycyclic scaffolds.
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