Nazarov Reactions of Vinyl Cyclopropylamines: An Approach to the Imino-Nazarov Problem

Nazarov Reactions of Vinyl Cyclopropylamines: An Approach to the Imino-Nazarov Problem

Dichlorocyclopropanation of 2-amino-1,3-dienes affords 1-alkenyl-1-amino-2,2-dichlorocyclopropanes which undergo silver-assisted 2-π electrocyclic opening to furnish 3-aminopentadienyl cations. Nazarov-type cyclization of these intermediates leads to cyclopentenone iminium salts, which provide allyl...

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Bibliographic Details
Published in:Organic letters Vol. 15; no. 11; pp. 2888 - 2891
Main Authors: Bonderoff, Sara A, Grant, Tina N, West, F. G, Tremblay, Martin
Format: Journal Article
Language:English
Published: United States American Chemical Society 07-06-2013
Subjects:
Catalysis
Cations - chemistry
Cyclization
Cyclopentanes - chemical synthesis
Cyclopentanes - chemistry
Cyclopropanes - chemistry
Molecular Structure
Silver - chemistry
Stereoisomerism
Vinyl Compounds - chemistry
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Summary:Dichlorocyclopropanation of 2-amino-1,3-dienes affords 1-alkenyl-1-amino-2,2-dichlorocyclopropanes which undergo silver-assisted 2-π electrocyclic opening to furnish 3-aminopentadienyl cations. Nazarov-type cyclization of these intermediates leads to cyclopentenone iminium salts, which provide allylic amines upon reduction. This process, the imino version of the traditional Nazarov reaction, can also be combined with an interrupted Nazarov domino process to give polycyclic amines.
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ISSN:1523-7060
1523-7052
DOI:10.1021/ol4012663