Insertion of Pyridine into the Calcium Allyl Bond: Regioselective 1,4-Dihydropyridine Formation and C----H Bond Activation

Insertion of Pyridine into the Calcium Allyl Bond: Regioselective 1,4-Dihydropyridine Formation and C----H Bond Activation

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‐a...

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Veröffentlicht in:Angewandte Chemie (International ed.) 2010-10, Vol.49 (42), p.7795-7798
Hauptverfasser: Jochmann, Phillip, Dols, Thomas S, Spaniol, Thomas P, Perrin, Lionel, Maron, Laurent, Okuda, Jun
Format: Artikel
Sprache:eng
Schlagworte:
Allyl Compounds - chemistry
allyl ligands
calcium
Calcium - chemistry
CC coupling
CH activation
density functional calculations
Dihydropyridines - chemical synthesis
Dihydropyridines - chemistry
Hydrogen Bonding
Molecular Structure
Organometallic Compounds - chemistry
Pyridines - chemistry
Stereoisomerism
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Zusammenfassung: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.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.201003704