Intramolecular [3 + 2]-Cycloadditions of Azomethine Ylides Derived from Secondary Amines via Redox-Neutral C–H Functionalization

Azomethine ylides are accessed under mild conditions via benzoic acid catalyzed condensations of 1,2,3,4-tetra­hydro­iso­quinolines or trypto­lines with aldehydes bearing a pendent dipolarophile. These intermediates undergo intramolecular [3 + 2]-cycloadditions in a highly diastereoselective fashion...

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Bibliographic Details
Published in:Organic letters 2014-11, Vol.16 (22), p.5910-5913
Main Authors: Mantelingu, Kempegowda, Lin, Yingfu, Seidel, Daniel
Format: Article
Language:English
Subjects:
Aldehydes - chemistry
Amines - chemical synthesis
Amines - chemistry
Azo Compounds - chemical synthesis
Azo Compounds - chemistry
Benzoic Acid - chemistry
Catalysis
Cyclization
Cycloaddition Reaction
Heterocyclic Compounds, 4 or More Rings - chemical synthesis
Heterocyclic Compounds, 4 or More Rings - chemistry
Letter
Molecular Structure
Oxidation-Reduction
Stereoisomerism
Tetrahydroisoquinolines - chemistry
Thiosemicarbazones - chemical synthesis
Thiosemicarbazones - chemistry
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Summary:Azomethine ylides are accessed under mild conditions via benzoic acid catalyzed condensations of 1,2,3,4-tetra­hydro­iso­quinolines or trypto­lines with aldehydes bearing a pendent dipolarophile. These intermediates undergo intramolecular [3 + 2]-cycloadditions in a highly diastereoselective fashion to form polycyclic amines with four new stereogenic centers. Challenging substrates such as piperidine, morpholine, and thiomorpholine undergo the corresponding reactions at elevated temperatures.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol502918g