1242612-16-3Relevant academic research and scientific papers
Synthesis of (-)-sedinine by allene cyclization and iminium Ion chemistry
Bates, Roderick W.,Lu, Yongna
supporting information; experimental part, p. 3938 - 3941 (2010/11/04)
A synthesis of the sedum alkaloid sedinine has been achieved employing silver(I)-catalyzed allenic hydroxylamine cyclization and ring-closing metathesis to form a bicyclic N,O-acetal. Ring opening of this acetal with a silyl enol ether under Lewis acidic conditions is exclusively trans selective, leading to the natural product after reduction. On the other hand, conversion of the bicyclic N,O-acetal to a semicyclic N,O-acetal results in no stereoselectivity during such a reaction. The contrasting results can be rationalized by consideration of the conformation of the iminium ions.
