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J Am Chem Soc. 2012 Jan 18;134(2):1352-6. doi: 10.1021/ja2105703. Epub 2011 Dec 14.

Three-component coupling sequence for the regiospecific synthesis of substituted pyridines.

Author information

1
Kellogg School of Science and Technology at The Scripps Research Institute, The Scripps Research Institute, Scripps Florida, Jupiter, Florida 33458, USA.

Abstract

A de novo synthesis of substituted pyridines is described that proceeds through nucleophilic addition of a dithiane anion to an α,β-unsaturated carbonyl followed by metallacycle-mediated union of the resulting allylic alcohol with preformed trimethylsilane-imines (generated in situ by the low-temperature reaction of lithium hexamethyldisilazide with an aldehyde) and Ag(I)- or Hg(II)-mediated ring closure. The process is useful for the convergent assembly of di- through penta-substituted pyridines with complete regiochemical control.

PMID:
22103772
PMCID:
PMC3262091
DOI:
10.1021/ja2105703
[Indexed for MEDLINE]
Free PMC Article

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