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Insertion of Pyridine into the Calcium Allyl Bond: Regioselective 1,4‐Dihydropyridine Formation and CH Bond Activation
Author(s) -
Jochmann Phillip,
Dols Thomas S.,
Spaniol Thomas P.,
Perrin Lionel,
Maron Laurent,
Okuda Jun
Publication year - 2010
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201003704
Subject(s) - chemistry , pyridine , regioselectivity , nucleophile , reagent , medicinal chemistry , dhps , stereochemistry , organic chemistry , catalysis , malaria , immunology , plasmodium falciparum , biology
The remarkable balance between nucleophilicity and basicity that is found for bis(allyl)calcium has not been previously reported for organolithium and organomagnesium reagents. Pyridine undergoes regioselective 1,4‐insertion into the calcium allyl bond of bis(allyl)calcium. The resulting calcium 4‐allyl‐1,4‐dihydropyridyl compound can be readily converted into the N‐protected 1,4‐dihydropyridine derivatives.