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Phosphine‐Catalyzed Synthesis of Chiral N ‐Heterocycles through (Asymmetric) P(III)/P(V) Redox Cycling
Author(s) -
Lorton Charlotte,
Saleh Nidal,
Voituriez Arnaud
Publication year - 2021
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.202100404
Subject(s) - chemistry , phosphine , enantiopure drug , phosphine oxide , phenylsilane , wittig reaction , catalysis , enantioselective synthesis , intramolecular force , medicinal chemistry , michael reaction , redox , combinatorial chemistry , stereochemistry , organic chemistry
Phosphine‐catalyzed tandem Michael addition/intramolecular Wittig reactions have been developed for the synthesis of chiral 2,5‐dihydro‐1 H ‐pyrrole and tetrahydropyridine derivatives. These processes have been rendered catalytic in phosphine, thanks to the in situ reduction of phosphine oxide by phenylsilane. Furthermore, catalytic and asymmetric P(III)/P(V) processes were implemented using enantiopure chiral phosphines.