Chemoselective functionalization of 3,3'-substituted BINOL derivatives.
An efficient chemoselective differentiation of vicinal phenolic and benzylic alcohols on optically active binaphthyl skeletons has been achieved via TBS protection of the less sterically hindered, external 3,3' benzylic positions. Further manipulation of functionalities either in the 2,2' or 3,3' positions is then easily achieved in high yields via the use of BOC protecting groups, functioning orthogonally to TBS.
Coluccini
Carmine
C
Department of Organic Chemistry, University of Pavia, Viale Taramelli 10, Pavia, Italy.
Castelluccio
Antonio
A
Pasini
Dario
D