Phosphine-catalyzed dearomative [3+2] cycloaddition of 4-nitroisoxazoles with allenoates or Morita–Baylis–Hillman carbonates
HE Yong-jun, Tian-Juan He, Xiufang Cheng, Yibo Wei, Huamin Wang, Ying‐Wu Lin
Abstract
An efficient phosphine-catalyzed dearomative [3+2] annulation of 4-nitroisoxazoles with allenoates or Morita-Baylis-Hillman carbonates has been established for the convenient synthesis of bicyclic isoxazoline derivatives. This reaction approach showed a broad substrate scope, high functional group compatibility, and excellent regioselectivity and diastereoselectivity. Furthermore, the success at the gram-scale and synthetic applications of the obtained compound 3a demonstrate the great potential of this methodology for practical applications in organic synthesis.
Topics & Concepts
CycloadditionPhosphineCatalysisChemistryCombinatorial chemistryOrganocatalysisMedicinal chemistryOrganic chemistryStereochemistryEnantioselective synthesisCatalytic C–H Functionalization MethodsCyclopropane Reaction MechanismsSynthesis and Catalytic Reactions