Additive-free synthesis of fused tricyclic cyanoisoxazolidines using <i>in situ</i> formed cyanonitrones
Muhammad Fahad Jamali, Usha Yadav, Mary Merlin Manjaly Babu, Ruchir Kant, Kishor Mohanan
Abstract
from diazoacetonitrile and nitrosoarene, and its subsequent [3+2] cycloaddition with oxabicyclic alkenes to access fused tricyclic cyanoisoxazolidines. Further, this methodology could be extended to access fused tricyclic trifluoromethylated and phosphonylated isoxazolidines. Surprisingly, the reductive ring-opening of cyanoisoxazolidines was followed by a spontaneous lactonization to produce fused tricyclic amino lactones. Moreover, the N-O bond of the obtained tricyclic trifluoromethylated isoxazolidines could be cleaved to obtain 1,3-amino alcohols.
Topics & Concepts
TricyclicChemistryIn situCycloadditionRing (chemistry)StereochemistryCombinatorial chemistryOrganic chemistryCatalysisCyclopropane Reaction MechanismsFluorine in Organic ChemistrySynthesis and Catalytic Reactions