Enantioselective Construction Of Spiro-Tetrahydroquinoline Scaffolds Through Asymmetric Catalytic Cascade Reactions

Jia-Lu Zhang, Rui Ma, Huan-Huan Zhao, Peng-Fei Xu

https://doi.org/10.1039/D2CC00502F

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.