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

Beddoe, Rhydian H.; Sneddon, Helen F.; Denton, Ross M.

Authors

Rhydian H. Beddoe

Helen F. Sneddon

ROSS DENTON ROSS.DENTON@NOTTINGHAM.AC.UK
Professor of Organic Chemistry



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.

Citation

Beddoe, R. H., Sneddon, H. F., & Denton, R. M. (2018). The catalytic Mitsunobu reaction: a critical analysis of the current state-of-the-art. Organic and Biomolecular Chemistry, 42(16), 7774-7781. https://doi.org/10.1039/c8ob01929k

Journal Article Type Article
Acceptance Date Sep 28, 2018
Online Publication Date Oct 1, 2018
Publication Date Nov 14, 2018
Deposit Date Oct 23, 2018
Publicly Available Date Oct 2, 2019
Journal Organic & Biomolecular Chemistry
Print ISSN 1477-0520
Electronic ISSN 1477-0539
Publisher Royal Society of Chemistry
Peer Reviewed Peer Reviewed
Volume 42
Issue 16
Pages 7774-7781
DOI https://doi.org/10.1039/c8ob01929k
Keywords Physical and Theoretical Chemistry; Organic Chemistry; Biochemistry
Public URL https://nottingham-repository.worktribe.com/output/1182665
Publisher URL https://pubs.rsc.org/en/Content/ArticleLanding/2018/OB/C8OB01929K#!divAbstract
Additional Information : This document is Similarity Check deposited; : Rhydian H. Beddoe (ORCID); : Ross M. Denton (ORCID); : Single-blind; : Received 7 August 2018; Accepted 28 September 2018; Accepted Manuscript published 1 October 2018; Advance Article published 11 October 2018

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