Tetrahedron Letters p. 3901 - 3904 (1995)
Update date:2022-07-29
Topics:
Carmen Bernabeu
The iodosulfonylation of (2E)-pentadienamides 1 affords stereoselectively (2E,4E)-5-tosylpentenamides 2. These dienic sulfones suffer nucleophilic vinylic substitution of the tosyl group by sodium thiolates and Grignard reagents to give regio- and stereo-selectively (2E,4E)-dienamides 3. This methodology has been applied to the synthesis of sarmentine (3bg) and an Achillea amide (3cg).
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(1995)
