Journal
ADVANCED SYNTHESIS & CATALYSIS
Volume 359, Issue 18, Pages 3108-3113Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/adsc.201700615
Keywords
Allenamide; gold; catalysis; hydride shift
Categories
Funding
- Ecole Polytechnique
- CNRS
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A new procedure for the synthesis of allenamides and structurally related compounds is reported. Under gold catalysis, a series of ynamides possessing a benzyloxy group at the propargylic position were efficiently converted into the corresponding allenamides following a 1,5 hydride shift process. The scope of the reaction was shown to be extremely broad allowing the formation of -mono or -disubstituted allenes possessing various functional groups. Notably, and in contrast to previously reported methods, not only N-allenyl sulfonamido but also urea, phosphonamido and the rarely studied phthalimido, pyrrolo, indolo and carbazolo derivatives could be readily and efficiently accessed.
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