Photogenerated quinone methides as useful intermediates in the synthesis of chiral BINOL ligands.
The photoinduced synthesis of chiral 3,3'-CH2X-disubstituted BINOL ligands (X = NR2, SR, OH) has been achieved with excellent ee by UV-visible activation of BINOLAMs bearing L-proline ester arms. Quinone methides, detected by laser flash photolysis, are the key intermediates involved in such a synthetic protocol, which undergo reversible nucleophilic conjugate additions by a great variety of nitrogen nucleophiles (amines and alpha-amino acid derivatives) with complete configuration retention of the BINOL moiety.
Colloredo-Mels
Stefano
S
Dipartimento di Chimica Organica, Università di Pavia, V.le Taramelli 10, 27100 Pavia, Italy.
Doria
Filippo
F
Verga
Daniela
D
Freccero
Mauro
M