Enantioselective phosphine-catalyzed [6 + 1] annulations of α-allyl allenoates with 1,1-bisnucleophiles
Jingxiong Lai, Wei Cai, You Huang
Abstract
a tandem γ-umpolung addition and δ'-addition process, smoothly constructing both seven-membered N-heterocycles and carbocycles with a broad scope of substrates, high atom economy and excellent enantioselectivity (up to 99% yield and up to 96% ee). Mechanistic experiments revealed a conversion of the 1,6-dipole into a 1,6-biselectrophilic intermediate through proton abstraction.
Topics & Concepts
PhosphineAnnulationEnantioselective synthesisReagentCatalysisAlleneChemistryCombinatorial chemistryOrganic chemistryMedicinal chemistryAsymmetric Synthesis and CatalysisAdvanced Synthetic Organic ChemistrySynthetic Organic Chemistry Methods