Phosphine-Catalyzed Tandem Annulation of Allenylic Alcohols with 1,1-Dicyanoalkenes
Zeqing Duan, Min Liu, Bing Zheng, Yi Tang, Juan Du, Lei Wang, Songcheng Yu, Yongjun Wu, Hongchao Guo
Abstract
The phosphine-catalyzed tandem annulation of allenylic alcohols with 1,1-dicyanoalkenes has been developed, giving various bicyclic tetrahydrocyclopentafuran derivatives in 40-89% yields with moderate to excellent diastereoselectivities. The fused ring was furnished through a sequential (3 + 2) annulation/nucleophilic addition reaction. The unusual nucleophilic addition of an alkoxide ion to a cyano group led to a formation of tetrahydrofuran ring having an imino substituent.
Topics & Concepts
AnnulationChemistryPhosphineNucleophileTandemSubstituentTetrahydrofuranRing (chemistry)CatalysisMedicinal chemistryAlkoxideNucleophilic additionBicyclic moleculeCombinatorial chemistryOrganic chemistrySolventComposite materialMaterials scienceAdvanced Synthetic Organic ChemistrySynthetic Organic Chemistry MethodsAsymmetric Synthesis and Catalysis