Enantioselective construction of spiro-tetrahydroquinoline scaffolds through asymmetric catalytic cascade reactions
Jialü Zhang, Rui Ma, Huanhuan Zhao, Peng‐Fei Xu
Abstract
An efficient and concise strategy has been successfully developed for merging spiro-tetrahydroquinoline with spiro-benzofuranone into a single new skeleton through asymmetric catalytic cascade reactions catalyzed by quinine-derived chiral bifunctional squaramide organocatalysts. In this approach, differently substituted spiro-tetrahydroquinoline derivatives were smoothly obtained with high yields, and excellent diastereoselectivities and enantioselectivities (up to 99% yield, up to >20 : 1 dr, up to >99% ee, 40 examples) under mild reaction conditions.
Topics & Concepts
SquaramideBifunctionalEnantioselective synthesisCatalysisYield (engineering)CascadeChemistryCombinatorial chemistryCascade reactionStereocenterReaction conditionsBifunctional catalystOrganocatalysisOrganic chemistryMaterials scienceChromatographyMetallurgyAsymmetric Synthesis and CatalysisAxial and Atropisomeric Chirality SynthesisSynthesis and Catalytic Reactions