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

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

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.

• Journal Article Type: Article
• Publication Date: Nov 14, 2018
• 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
• APA6 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. doi:10.1039/c8ob01929k
• DOI: https://doi.org/10.1039/c8ob01929k
• Keywords: Physical and Theoretical Chemistry; Organic Chemistry; Biochemistry
• 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