Gold-Catalyzed Cyclization/Hydroboration of 1,6-Enynes: Synthesis of Bicyclo[3.1.0]hexane Boranes
Guanghui Wang, Yong‐Qiang Wang, Zengzeng Li, Haotian Li, Mingwu Yu, Maofu Pang, Ximei Zhao
Abstract
The gold-catalyzed cyclization/hydroboration of 1,6-enynes offers facile, versatile, and atom-economical one-step access to bicyclo[3.1.0]hexane boranes. This new protocol proceeds in moderate to good yields under mild conditions. Different from bicyclo[3.1.0]hexane borates, these products are stable in air and during chromatography. Moreover, the borane moiety of the products can readily undergo a diverse array of transformations. The kinetic isotope effect experiment indicates that the hydrogen-transfer step is a fast process, which is not involved in the rate-limiting step.
Topics & Concepts
HydroborationChemistryBoranesBicyclic moleculeHexaneMoietyCatalysisBoraneCombinatorial chemistryDiboraneOrganic chemistryBoronCatalytic Alkyne ReactionsOrganoboron and organosilicon chemistryAsymmetric Hydrogenation and Catalysis