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.
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11571/108118
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