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Polymer‐Supported Hantzsch 1,4‐Dihydropyridine Ester: An Efficient Biomimetic Hydrogen Source for the Reduction of Ketimines and Electron‐Withdrawing Group Conjugated Olefins
Author(s) -
Che Jun,
Lam Yulin
Publication year - 2010
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201000093
Subject(s) - chemistry , conjugated system , dihydropyridine , polar effect , cyclopropane , polymer , organic chemistry , combinatorial chemistry , ring (chemistry) , calcium
A polymer‐supported Hantzsch 1,4‐dihydropyridine ester was observed to be a useful selective reducing agent for the reduction of ketimines and electron‐withdrawing conjugated olefins. The rate of the reduction of electron‐withdrawing conjugated olefins is dependent on the nature of the conjugated substituents and could be enhanced by microwave irradiation. The reduction of ( Z )‐α‐cyano‐β‐bromomethylcinnamates to cyclopropane derivatives using polymer‐supported Hantzsch 1,4‐dihydropyridine ester was found to proceed stereoselectively and in good yields.