109838-89-3Relevant articles and documents
Synthesis of Azabicycles via Cascade Aza-Prins Reactions: Accessing the Indolizidine and Quinolizidine Cores
Chio, Freda K. I.,Guesné, Sébastien J. J.,Hassall, Lorraine,McGuire, Thomas,Dobbs, Adrian P.
, p. 9868 - 9880 (2015/11/03)
The first detailed studies of intramolecular aza-Prins and aza-silyl-Prins reactions, starting from acyclic materials, are reported. The methods allow rapid and flexible access toward an array of [6,5] and [6,6] aza-bicycles, which form the core skeletons of various alkaloids. On the basis of our findings on the aza-Prins and aza-silyl-Prins cyclizations, herein we present simple protocols for the intramolecular preparation of the azabicyclic cores of the indolizidines and quinolizidines using a one-pot cascade process of N-acyliminium ion formation followed by aza-Prins cyclization and either elimination or carbocation trapping. It is possible to introduce a range of different substituents into the heterocycles through a judicial choice of Lewis acid and solvent(s), with halo-, phenyl-, and amido-substituted azabicyclic products all being accessed through these highly diastereoselective processes.
A versatile indium trichloride mediated Prins-type reaction to unsaturated heterocycles
Dobbs, Adrian P.,Guesne, Sebastien J. J.,Martinovic, Sasa,Coles, Simon J.,Hursthouse, Michael B.
, p. 7880 - 7883 (2007/10/03)
A versatile and high-yielding indium trichloride mediated cyclization reaction of silylated homoallylic alcohols, thiols, or amines with aldehydes or epoxides is described as a rapid route to a range of unsaturated heterocycles. The excellent diastereosel
