Open AccessRedox-neutral organocatalytic Mitsunobu reactions
Author(s) -
Rhydian H. Beddoe,
Keith G. Andrews,
Valentin Magné,
James D. Cuthbertson,
Jan Saska,
Andrew L. Shan-Little,
Stephen E. Shanahan,
Helen F. Sneddon,
Ross M. Denton
Publication year - 2019
Publication title -
science
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 12.556
H-Index - 1186
eISSN - 1095-9203
pISSN - 0036-8075
DOI - 10.1126/science.aax3353
Subject(s) - phosphine , chemistry , phosphine oxide , substituent , mitsunobu reaction , alcohol , redox , combinatorial chemistry , medicinal chemistry , organic chemistry , catalysis
Displacing OH groups catalytically The Mitsunobu reaction is widely used to invert the configuration of alcohols. However, its major drawback is the need to activate the alcohol with a full equivalent of phosphine, thereby generating a phosphine oxide co-product. Beddoeet al. report a phosphine oxide compound that achieves the same result catalytically (see the Perspective by Longwitz and Werner). The key is a phenol substituent that can reversibly bond through its oxygen to phosphorus, forming a ring that the alcohol opens. The phosphorus thus remains in the +5 oxidation state throughout the reaction, and water is the only by-product.Science , this issue p.910 ; see also p.866
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