An efficient and practical entry to 2-amido-dienes and 3-amido-trienes from allenamides through stereoselective 1,3-hydrogen shifts

Preparations of de novo acyclic 2-amido-dienes and 3-amido-trienes through 1,3-hydrogen shifts from allenamides are described. These 1,3-hydrogen shifts could be achieved thermally or they could be promoted by the use of Brønsted acids. Under either condition, these processes are highly regioselecti...

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Veröffentlicht in:Beilstein journal of organic chemistry 2011-04, Vol.7 (1), p.410-420
Hauptverfasser: Hayashi, Ryuji, Feltenberger, John B, Lohse, Andrew G, Walton, Mary C, Hsung, Richard P
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Sprache:eng
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Zusammenfassung:Preparations of de novo acyclic 2-amido-dienes and 3-amido-trienes through 1,3-hydrogen shifts from allenamides are described. These 1,3-hydrogen shifts could be achieved thermally or they could be promoted by the use of Brønsted acids. Under either condition, these processes are highly regioselective in favour of the α-position, and highly stereoselective in favour of the E-configuration. In addition, 6π-electron electrocyclic ring-closure could be carried out with 3-amido-trienes to afford cyclic 2-amido-dienes, and such electrocyclic ring-closure could be rendered in tandem with the 1,3-hydrogen shift.
ISSN:1860-5397
1860-5397
DOI:10.3762/bjoc.7.53