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HERO ID
7035719
Reference Type
Journal Article
Title
The catalytic Mitsunobu reaction: a critical analysis of the current state-of-the-art
Author(s)
Beddoe, RH; Sneddon, HF; Denton, RM; ,
Year
2018
Is Peer Reviewed?
1
Journal
Organic and Biomolecular Chemistry
ISSN:
1477-0520
EISSN:
1477-0539
Publisher
ROYAL SOC CHEMISTRY
Location
CAMBRIDGE
Page Numbers
7774-7781
Language
English
PMID
30306184
DOI
10.1039/c8ob01929k
Web of Science Id
WOS:000448947100001
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.
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