Trifluoroacetic acid-mediated intramolecular formal NH insertion reactions with amino-α-diazoketones: a facile and efficient synthesis of optically pure pyrrolidinones …

H Yang, V Jurkauskas, N Mackintosh…

文献索引：Yang, Hua; Jurkauskas, Valdas; Mackintosh, Nicole; Mogren, Tobias; Stephenson, Corey R. J.; Foster, Katherine; Brown, William; Roberts, Edward Canadian Journal of Chemistry, 2000 , vol. 78, # 6 p. 800 - 808

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被引用次数: 12

摘要

Trifluoroacetic acid (TFA) was found to promote intramolecular formal NH insertion reactions. Upon treatment with TFA, optically pure N-Boc-β'-amino-α-diazoketones (5a-c) and N-Boc-γ'-amino-α-diazoketones (10a-d) can be converted, with retention of chirality, into pyrrolidinones (11a-c) and piperidinones (12a-d), respectively, with concomitant removal of the Boc group, in good to excellent yields. Key words: α-diazoketone, amino acid, ...