6533b861fe1ef96bd12c4321

RESEARCH PRODUCT

ChemInform Abstract: Asymmetric Allylation/Pauson-Khand Reaction: A Simple Entry to Polycyclic Amines. Application to the Synthesis of Aminosteroid Analogues.

Antoni RieraAntonio Simón-fuentesSantos FusteroPablo BarrioRuben LazaroNuria Aiguabella

subject

Chemistrymedicine.medical_treatmentIntramolecular forcePauson–Khand reactionmedicineSonogashira couplingGeneral MedicineCombinatorial chemistryAminosteroidmedicine.drugSteroid

description

Asymmetric allylation of o-iodoarylsulfinylimines has been achieved in high diastereoselectivities. The thus-obtained o-iodoarylhomoallylic sulfinamides participate in a subsequent Sonogashira coupling followed by a diastereoselective intramolecular Pauson–Khand reaction. In this way, tricyclic amines showing a unique benzo-fused indenyl backbone were obtained. The methodology has been applied to the synthesis of amino steroid analogues.

https://doi.org/10.1002/chin.201432025