6253-24-3Relevant articles and documents
OLEFIN CYCLISATIONS OF HINDERED α-ACYLIMINIUM IONS
Wijnberg, B. P.,Speckamp, W. N.,Oostveen, A. R. C.
, p. 209 - 217 (1982)
Stereocontrolled NaBH4/H+-reduction of 3,4-cis-disubstituted N-alkenyl imides 1-5 leads to secondary hydroxylactams.Tertiary hydroxylactams are formed via addition of MeMgCl to imides 2 and 4.HCOOH-Cyclisation of the hydroxylactams affords polycyclic piperidines through stereoselective α-acyliminium ring closure.Concomitant synchronous and stepwise cyclisation pathways are operative in the anti-periplanar addition of tertiary α-acyliminium ions to Me substituted olefins 8c and 11c.