Palladium-Catalyzed [3,3]-Rearrangement for the Facile Synthesis of Allenamides

A [3,3]-rearrangement that is used for facile construction of chiral allenamides is described. A propargylic alcohol, a chlorophosphite, and Cbz-azide are combined to provide a propargylic phosphorimidate that, in the presence of catalytic palladium(II), rearranges to an allenamide. By varying the s...

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Bibliographic Details
Published in:Organic letters 2010-06, Vol.12 (11), p.2574-2577
Main Authors: Danowitz, Amy M., Taylor, Christopher E., Shrikian, Tamar M., Mapp, Anna K.
Format: Article
Language:English
Subjects:
Alkynes - chemistry
Amides - chemical synthesis
Amides - chemistry
Catalysis
Combinatorial Chemistry Techniques
Molecular Structure
Palladium - chemistry
Phosphites - chemistry
Propanols - chemistry
Stereoisomerism
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Summary:A [3,3]-rearrangement that is used for facile construction of chiral allenamides is described. A propargylic alcohol, a chlorophosphite, and Cbz-azide are combined to provide a propargylic phosphorimidate that, in the presence of catalytic palladium(II), rearranges to an allenamide. By varying the substitution pattern on the propargylic alcohol, mono-, di-, and trisubstituted allenamides can be accessed in good yields. Additionally, the use of an enantiomerically enriched propargylic alcohol enables the preparation of stereochemically defined allenamides.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol1007845