Gold-Catalyzed Addition–<i>N</i>-Boc Cleavage–Cyclization of <i>N</i>,<i>O</i>-Acetal with Ynamides for Construction of 6-(<i>tert</i>-Butyldimethylsilyl)oxy-tetrahydropyrrolo[1,2-<i>c</i>][1,3]oxazin-1-ones
Yan-Xue Zhang, Ling‐Yan Chen, Jian‐Ting Sun, Yuying Zhang, Bang‐Guo Wei
Abstract
A highly efficient gold-catalyzed approach between N,O-acetals and ynamides for the construction of 6-(tert-butyldimethylsilyl)oxy-tetrahydropyrrolo[1,2-c][1,3]oxazin-1-ones was developed. This reaction tolerated a wide range of substituted N,O-acetals and TsN-substituted ynamides, leading to novel heterocycles in moderate to good yields and with excellent diastereoselectivities (dr > 99:1).
Topics & Concepts
ChemistryAcetalCatalysisCleavage (geology)Combinatorial chemistryStereochemistryMedicinal chemistryOrganic chemistryFracture (geology)EngineeringGeotechnical engineeringCatalytic Alkyne ReactionsCyclopropane Reaction MechanismsCatalytic C–H Functionalization Methods