1411894-73-9Relevant articles and documents
Diastereoselective multicomponent cascade reaction leading to [3.2.0]-heterobicyclic compounds
Ausmees, Kerti,Kriis, Kadri,Pehk, T?nis,Werner, Franz,Jaì?rving, Ivar,Lopp, Margus,Kanger, T?nis
, p. 10680 - 10687 (2013/02/22)
A general three-component triple cascade reaction through an iminiuma-enaminea-iminium sequential activation initiated by a hetero-Michael addition to α,β-unsaturated aldehydes affords [3.2.0]heterobicycles in high diastereoselectivity. The rate and diastereoselectivity of the reaction depended on the (E)-4-heterocrotonate and size of the secondary amine. The enantiomers of the major diastereoisomer of oxa-and azabicyclo[3.2.0]heptane derivatives were separated by enzymatic kinetic resolution with immobilized Candida antarctica Lipase B (CALB), with E values up to 153. The absolute configuration of the nonacylated enantiomer of oxabicyclo[3.2.0]heptane was determined by single crystal X-ray analysis.