期刊
CHEMISTRY-A EUROPEAN JOURNAL
卷 23, 期 3, 页码 513-518出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201604356
关键词
asymmetric synthesis; aza-Diels-Alder reaction; organocatalysis; piperidones; silylketene acetals
资金
- Deutsche Forschungsgemeinschaft [SCHN 441/ 10-1]
We disclose herein the first enantioselective aza-Diels-Alder reaction of beta-alkyl-substituted vinylketene silyl-O,O-acetals and imines furnishing a broad range of optically highly enriched 4-alkyl-substituted 2-piperidones. As a catalyst for this one-pot reaction we employed a chiral phosphoric acid which effects a vinylogous Mannich reaction directly followed by ring-closure to the lactam. Subsequent fully diastereoselective transformations including hydrogenation, enolate alkylation, and lactam alkylation/reduction processes converted the cyclo-adducts into various highly substituted piperidines of great utility for the synthesis of natural products and medicinally active compounds.
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