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Preparation and Reactivity of Acyclic Chiral Allylzinc Species by a Zinc‐Brook Rearrangement
Author(s) -
Leibeling Markus,
Shurrush Khriesto A.,
Werner Veronika,
Perrin Lionel,
Marek Ilan
Publication year - 2016
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.201602393
Subject(s) - electrophile , chirality (physics) , cope rearrangement , zinc , stereochemistry , chemistry , reactivity (psychology) , walden inversion , sequence (biology) , transition state , catalysis , organic chemistry , physics , chiral symmetry , medicine , biochemistry , alternative medicine , pathology , quantum mechanics , nambu–jona lasinio model , quark
The zinc‐Brook rearrangement of enantiomerically enriched α‐hydroxy allylsilane produces a chiral allylzinc intermediate, which reacts with retention of configuration in the presence of an electrophile. Two remarkable features of this transformation are the stereochemical outcome during the formation of the allylzinc species and the complete stereocontrol in the organized six‐membered transition state, which leads to an overall and complete transfer of chirality within the reaction sequence.