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 R-amino acid derivatives) with complete configuration retention of the BINOL moiety.
Photogenerated Quinone Methides as Useful Intermediates in the Synthesis of Chiral Binol Ligands
DORIA, FILIPPO;VERGA, DANIELA;FRECCERO, MAURO
2006-01-01
Abstract
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 R-amino acid derivatives) with complete configuration retention of the BINOL moiety.File in questo prodotto:
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