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Titanium-Mediated Spirocyclization Reactions of 4-Alkylpyridines
Journal article   Peer reviewed

Titanium-Mediated Spirocyclization Reactions of 4-Alkylpyridines

Sharavathi G Parameswarappa and F. Christopher Pigge
Organic letters, Vol.12(15), pp.3434-3437
08/06/2010
DOI: 10.1021/ol1012636
PMID: 20670009

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Abstract

Pyridines substituted at the 4-position with alkyl tethers containing β-dicarbonyl moieties were converted to spirocyclic 4,4-disubstituted dihydropyridines. Optimal conditions for these transformations involved N-acylation of the pyridine substrate with a chloroformate electrophile in the presence of Ti(OiPr)4. Cyclization products could be easily converted into spiro-piperidine derivatives or elaborated into more complex heterocyclic frameworks via Au-catalyzed cycloisomerization.

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