Tetrahedron p. 13857 - 13864 (1994)
Update date:2022-08-17
Topics:
De Ancos, Begona
Carmen Maestro
Rosano Martin
Mateo, Ana I.
Reaction conditions and structure of the starting enamines (cyclic or open-chain) determine greatly the final products of the title reactions. Whereas in benzene and acetonitrile, DMAD and 1 give a mixture of the diastereoisomeric dienamines 5, in methanol they afford pirrolizine 3. Enaminofuranones 2 and 10 furnish in the corresponding 'Michael adducts' 7a,b,c and 11a,b,c but fail to yield pirrolizines. It has been demonstrated that above b and c adducts differ exclusively on the arrangement of groups around a chiral axis.
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