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Intermolecular Stereospecific Substitution of Underivatized Enantioenriched Secondary Alcohols by Organocatalysis
Author(s) -
Akkarasamiyo Sunisa,
Samec Joseph S. M.
Publication year - 2019
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201911532
Subject(s) - allylic rearrangement , stereospecificity , chemistry , organocatalysis , substitution (logic) , organic chemistry , intermolecular force , catalysis , substitution reaction , combinatorial chemistry , enantioselective synthesis , molecule , computer science , programming language
The stereospecific substitution of non‐derivatized and non‐allylic enantioenriched alcohols with only water as a by‐product would enable the use of readily available alcohols as substrates for green and sustainable transformations. However, the poor leaving group ability of the OH group has hampered the development of such a process. Denton and co‐workers recently described the use of (2‐hydroxybenzyl)diphenylphosphine oxide as a catalyst of a redox‐neutral and zero‐waste‐generating Mitsunobu reaction. This innovative process constitutes the first intermolecular stereospecific substitution of non‐allylic alcohols, and might find industrial applications.