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Diastereoselective Synthesis of Open‐Chain Secondary Alkyllithium Compounds and Trapping Reactions with Electrophiles
Author(s) -
Dagousset Guillaume,
Moriya Kohei,
Mose Rasmus,
Berionni Guillaume,
Karaghiosoff Konstantin,
Knochel Paul
Publication year - 2014
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.201308679
Subject(s) - synthon , electrophile , chemistry , stereoselectivity , reagent , lithium (medication) , combinatorial chemistry , alkyl , iodide , organic chemistry , catalysis , medicine , endocrinology
A practical stereoselective iodide–lithium exchange was used in the first general preparation of functionalized stereodefined acyclic secondary nonstabilized lithium reagents from the corresponding secondary alkyl iodides. These lithium reagents react with various electrophiles including carbon electrophiles with high retention of configuration. Kinetic data on the configurational stability of these acyclic alkyllithium reagents are given. This methodology offers a new entry to chiral synthons for the stereoselective synthesis of open‐chain molecules.