The catalytic Mitsunobu reaction: a critical analysis of the current state-of-the-art. Issue 42 (11th October 2018)

• Record Type: Journal Article
• Authors: Beddoe, Rhydian H.; Sneddon, Helen F.; Denton, Ross M.
• Is Part Of: Organic & biomolecular chemistry. Volume 16:Issue 42(2018)
• Page Start: 7774
• Page End: 7781
• Publication Date: 2018-10-11
• Subjects: Chemistry, Organic -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1039/c8ob01929k
• Languages: English
• ISSNs: 1477-0520

Abstract

Abstract : This Review article provides a summary and critical metrics-based analysis of recently developed catalytic Mitsunobu reactions. 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.