6533b85bfe1ef96bd12bb405
RESEARCH PRODUCT
Enantiospecific Brook Rearrangement of Tertiary Benzylic α-Hydroxysilanes
Valentin Paul NicuValentin Paul NicuWybren Jan BumaJuana M. PérezYiyin XiaSyuzanna R. HarutyunyanMark A. J. KoenisJuan F. ColladosPablo Ortizsubject
Acylation010405 organic chemistryChemistryStereochemistryOrganic ChemistryElectrophileAbsolute configurationPhysical and Theoretical ChemistryBrook rearrangement010402 general chemistryChirality (chemistry)01 natural sciences0104 chemical sciencesdescription
The Brook rearrangement of simple, chiral tertiary benzylic -hydroxysilanes is presented. The rearrangement followed by proton trapping is enantiospecific and proceeds with inversion of the configuration at the carbon center. Importantly, the [1,2]-Brook rearrangement can be followed by trapping of methyl or allyl electrophiles even in the protic environment, although with minimal retention of chirality.
| year | journal | country | edition | language |
|---|---|---|---|---|
| 2018-01-19 | European Journal of Organic Chemistry |