Chiral Phosphoric Acid Catalyzed Enantioselective [4+3]-Cyclization Reaction of Indol-4-ylmethanols and Quinone Esters
Xufeng Lin, Zhouli Chen, Lei Wang, Yiheng Qian
Abstract
Abstract An asymmetric [4+3]-cyclization reaction of racemic indol-4-ylmethanols and quinone esters catalyzed by chiral phosphoric acids has been developed. This method provides efficient access to biologically important [1]benzoxepino[5,4,3-cd]indoles featuring both axial and central chirality in good yields and up to 98% ee, as essentially single diastereomers, under mild reaction conditions.
Topics & Concepts
ChemistryDiastereomerEnantioselective synthesisPhosphoric acidQuinoneCatalysisChirality (physics)Organic chemistryReaction conditionsBrønsted–Lowry acid–base theoryCombinatorial chemistryStereochemistryNambu–Jona-Lasinio modelChiral symmetry breakingQuarkPhysicsQuantum mechanicsAxial and Atropisomeric Chirality SynthesisSynthesis of Indole DerivativesAlkaloids: synthesis and pharmacology