Stereospecific and Stereodivergent Construction of Quaternary Carbon Centers through Switchable Directed/Nondirected Allylic Substitution | Zendy

Breit Bernhard | Zendy; Demel Peter | Zendy; Studte Christopher | Zendy

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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).

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