The “Fully Catalytic System” in Mitsunobu Reaction Has Not Been Realized Yet

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• 作者：Daisuke Hirose ; Martin Gazvoda ; Janez Košmrlj ; Tsuyoshi Taniguchi
• 刊名：Organic Letters
• 出版年：2016
• 出版时间：August 19, 2016
• 年：2016
• 卷：18
• 期：16
• 页码：4036-4039
• 全文大小：265K
• 年卷期：0
• ISSN：1523-7052

文摘

An investigation of the recently reported “fully catalytic Mitsunobu reaction” using catalytic amounts of a phosphine reagent and an azo reagent has shown that although benzyl 4-nitrobenzoate is formed under the fully catalytic conditions, the same result is obtained if the hydrazine catalyst is omitted, indicating that this is not a Mitsunobu reaction. In addition, when the reaction between (−)-ethyl lactate and 4-nitrobenzoic acid was carried out using the “fully catalytic” method, the corresponding ester was formed but in very low yield and with predominant retention of configuration. Unfortunately, the system catalytic in phosphine reagent is incompatible with that in the azo reagent.