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Stereocontrolled synthesis of conjugated dienamides via the ynamine-claisen rearrangement with (arylthio)ynamine

✍ Scribed by Takeshi Nakai; Hiroyuki Setoi; Yasuhide Kageyama

Publisher: Elsevier Science
Year: 1981
Tongue: French
Weight: 244 KB
Volume: 22
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(01)82075-x

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✦ Synopsis

dienamides is described which relies upon the acid-catalyzed or therma ynamine-CZaisen rearrangement with readiZy accessible laryZthiolynamines. The Claisen rearrangement has found substantial utility in the methodology of synthetic organic chemistry.2) For example, the reaction of an allylic alcohol with ynamines affords the rearranged y,&unsaturated amides via the ketene N,O-acetal intermediates in the so-called ynamine-Claisen rearrangement first developed by Ficini. 3) More recently Bartlett has reported interesting stereochemical features of the Claisen variant. 4) We have recently developed an exceedingly convenient method for preparing (arylthio)ynamines (3 from 2,2,2-trifluoroethyl sulfides and secondary amines. 5) Thus the easy availability ofJ, coupled with our continuing interest in synthetic applications of sigmatropic rearrangements, 6) prompted us to examine the unexplored ynamine-Claisen rearrangement with L.

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