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J Am Chem Soc. 2013 Feb 20;135(7):2478-81. doi: 10.1021/ja312311k. Epub 2013 Feb 11.

Unstabilized azomethine ylides for the stereoselective synthesis of substituted piperidines, tropanes, and azabicyclo[3.1.0] systems.

Author information

1
Department of Chemistry, Yale University, New Haven, Connecticut 06520, USA.

Abstract

Acid treatment of densely substituted 2-silyl-1,2-dihydropyridines provides a new and convenient entry to reactive azomethine ylides that can (1) be protonated and reduced with high stereoselectivity to give piperidines, (2) participate in [3 + 2] dipolar cycloaddition to give tropanes, and (3) undergo a Nazarov-like 6-π electrocyclization that upon reduction give 2-azabicyclo[3.1.0] systems.

PMID:
23398467
PMCID:
PMC3586708
DOI:
10.1021/ja312311k
[Indexed for MEDLINE]
Free PMC Article

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