The "Fully Catalytic System" in Mitsunobu Reaction Has Not Been Realized Yet
Daisuke Hirose1, Martin Gazvoda2, Janez Košmrlj2
1Graduate School of Natural Science and Technology, Kanazawa University , Kakuma-machi, Kanazawa 920-1192, Japan.
Abstract:
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.
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