Premium
Brook Rearrangement as a Trigger for the Ring Opening of Strained Carbocycles
Author(s) -
Zhang FaGuang,
Eppe Guillaume,
Marek Ilan
Publication year - 2016
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201510094
Subject(s) - diastereomer , chemistry , stereoselectivity , enantiomer , silane , cleavage (geology) , ring (chemistry) , bond cleavage , stereochemistry , medicinal chemistry , organic chemistry , catalysis , materials science , fracture (geology) , composite material
The combined regio‐ and stereoselective carbometalation of cyclopropenyl amides, followed by the addition of an acyl silane, led to the formation of polysubstituted cyclopropyl derivatives as unique diastereoisomers. Upon warming of the reaction mixture to room temperature, a Brook rearrangement proceeded with inversion of configuration to provide ready access to δ‐ketoamides possessing a quaternary carbon center with high enantiomeric ratios through selective CC bond cleavage of the ring.