Asymmetric synthesis of highly functionalized spirothiazolidinone tetrahydroquinolines: Via a squaramide-catalyzed cascade reaction

Yong Xing Song, Da Ming Du*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

21 Citations (Scopus)

Abstract

A bifunctional squaramide-catalyzed asymmetric cascade aza-Michael/Michael addition reaction for the synthesis of chiral spirothiazolidinone tetrahydroquinolines with three contiguous stereocenters has been developed. This cascade reaction proceeded well under mild conditions, and afforded the desired products in high to excellent yields (up to >99% yield) with excellent diastereoselectivities (>25:1 dr) and high enantioselectivities (up to 96% ee). More importantly, both the amplification and the derivation experiments do not affect the stereoselectivity.

Original languageEnglish
Pages (from-to)9390-9401
Number of pages12
JournalOrganic and Biomolecular Chemistry
Volume16
Issue number48
DOIs
Publication statusPublished - 2018

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Song, Y. X., & Du, D. M. (2018). Asymmetric synthesis of highly functionalized spirothiazolidinone tetrahydroquinolines: Via a squaramide-catalyzed cascade reaction. Organic and Biomolecular Chemistry, 16(48), 9390-9401. https://doi.org/10.1039/c8ob02731e