Origins of Selectivity in Br酶nsted Acid-Promoted Diazoalkane鈭扐zomethine Reactions (The Aza-Darzens Aziridine Synthesis)

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• 作者：Timothy L. Troyer ; Hubert Muchalski ; Ki Bum Hong ; Jeffrey N. Johnston
• 刊名：Organic Letters
• 出版年：2011
• 出版时间：April 1, 2011
• 年：2011
• 卷：13
• 期：7
• 页码：1790-1792
• 全文大小：723K
• 年卷期：v.13,no.7(April 1, 2011)
• ISSN：1523-7052

文摘

The mechanism of the Br酶nsted acid-catalyzed aza-Darzens reaction is explored by charting the stereochemical outcome of the triflic acid-promoted conversion of trans-triazolines to cis-aziridines. These experiments are consistent with the intermediacy of an 伪-diazonium-尾-amino ester intermediate.