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Stereospecific and Stereodivergent Construction of Quaternary Carbon Centers through Switchable Directed/Nondirected Allylic Substitution
Author(s) -
Breit Bernhard,
Demel Peter,
Studte Christopher
Publication year - 2004
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.200453991
Subject(s) - stereospecificity , substitution (logic) , allylic rearrangement , chirality (physics) , quaternary carbon , chemistry , substitution reaction , reagent , selectivity , stereochemistry , enantioselective synthesis , organic chemistry , catalysis , computer science , symmetry breaking , spontaneous symmetry breaking , physics , programming language , quantum mechanics , nambu–jona lasinio model
Selectivity at the flick of a switch: Through 1,3‐chirality transfer, a directing/nondirecting leaving group facilitates the stereospecific and stereodivergent construction of quaternary carbon centers by copper‐mediated allylic substitution with Grignard and organozinc reagents (see scheme; the use of the corresponding phosphane oxide leads to selective anti substitution).