SCOPE OF [1+2+3] ANNULATIONS USING AMINONITRILES AS MICHAEL DONORS

The reaction of (NN-dimethylamino)phenylacetonitrile anion (1) as a on e-carbon atom Michael donor toward alpha,beta-unsaturated lactones and ketones followed by allylation of the intermediate enolates provided in a one-pot procedure trans alpha-monoallylated beta-substituted lact ones and cyclanones 4a-d, 5, and 6b. Attempts at cyclization of compou nds 4a-d and 5b, with the cyano moiety being the leaving group, were u nsuccessful. The only successful [1 + 2 + 3] hexannulation giving N,N- dimethylamino trans ring-fused bicyclic lactone 12b was run with 6b be aring an allylic silane moiety.