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.
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Jochmann et al. (2010) studied this question.
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