Tetrahedron

DMEAD: a new dialkyl azodicarboxylate for the Mitsunobu reaction

K Hagiya, N Muramoto, T Misaki, T Sugimura

Index: Hagiya, Kazutake; Muramoto, Natsuko; Misaki, Tomonori; Sugimura, Takashi Tetrahedron, 2009 , vol. 65, # 31 p. 6109 - 6114

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Citation Number: 32

Abstract

Di-2-methoxyethyl azodicarboxylate (DMEAD) is prepared in 65% yield in two steps as a crystalline solid. Use of DMEAD in the Mitsunobu reaction of a variety of alcohols with pronucleophiles results in good yields of the products under sufficient stereospecificity of inversion, as conventional diisopropyl azodicarboxylate (DIAD) does. Isolation of the product is, however, much easier with DMEAD than that with DIAD, because the hydrazine ...

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