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Issue 42, 2018
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The catalytic Mitsunobu reaction: a critical analysis of the current state-of-the-art

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Abstract

The Mitsunobu reaction is widely regarded as the pre-eminent method for performing nucleophilic substitutions of alcohols with inversion of configuration. However, its applicability to large-scale synthesis is undermined by the fact that alcohol activation occurs at the expense of two stoichiometric reagents – a phosphine and an azodicarboxylate. The ideal Mitsunobu reaction would be sub-stoichiometric in the phosphine and azodicarboxylate species and employ innocuous terminal oxidants and reductants to achieve recycling. This Review article provides a summary and analysis of recent advances towards the development of such catalytic Mitsunobu reactions.

Graphical abstract: The catalytic Mitsunobu reaction: a critical analysis of the current state-of-the-art

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Article information


Submitted
07 Aug 2018
Accepted
28 Sep 2018
First published
01 Oct 2018

Org. Biomol. Chem., 2018,16, 7774-7781
Article type
Review Article

The catalytic Mitsunobu reaction: a critical analysis of the current state-of-the-art

R. H. Beddoe, H. F. Sneddon and R. M. Denton, Org. Biomol. Chem., 2018, 16, 7774
DOI: 10.1039/C8OB01929K

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