New stereoselective synthesis of trienes

Identifier:  TFG:6574

Handle: https://hdl.handle.net/20.500.11797/TFG6574

Authors:  Iragorri Molinero, Nerea

Abstract:
A new stereoselective synthesis of conjugated trienamides by means of an anionic cascade reaction has been reported when testing the influence of the sterics of the anion-accelerated amino-Cope reaction. By the direct g-selective union of a dienolate and a chiral conjugated sulfinyl imine containing bulky groups, a product containing a 3-double bonds conjugated system is obtained. This contrasts with the six-membered ring product obtained when the same reaction is performed with non-sterically hindered compounds. The same reaction was tested with chiral non-conjugated sulfinyl imines, and a 2-double bonds conjugated system product was obtained.