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Enantiospecific Brook Rearrangement of Tertiary Benzylic α‐Hydroxysilanes
Author(s) -
Collados Juan F.,
Ortiz Pablo,
Pérez Juana M.,
Xia Yiyin,
Koenis Mark A. J.,
Buma Wybren J.,
Nicu Valentin P.,
Harutyunyan Syuzanna R.
Publication year - 2018
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201701469
Subject(s) - chemistry , electrophile , chirality (physics) , cope rearrangement , trapping , carroll rearrangement , walden inversion , stereochemistry , sigmatropic reaction , organic chemistry , catalysis , chiral symmetry , nuclear physics , ecology , physics , nambu–jona lasinio model , biology , quark
The Brook rearrangement of simple, chiral tertiary benzylic α‐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.