Enantioselective Squaramide-Catalyzed Trifluoromethylthiolation-Sulfur-Michael/Aldol Cascade Reaction: One-Pot Synthesis of CF3S-Containing Spiro Cyclopentanone-Thiochromanes

Bo Liang Zhao, Da Ming Du*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

56 Citations (Scopus)

Abstract

A novel bifunctional squaramide-catalyzed one-pot electrophilic trifluoromethylthiolation-sulfur-Michael/aldol cascade reaction for the construction of CF3S-containing spiro-cyclopentanone-thiochromanes was developed. This convenient, one-pot cascade reaction serves as a powerful tool for the enantioselective construction of potential bioactive spiro-cyclopentanone-thiochromanes, which have one quaternary stereocenter containing a CF3S group and three contiguous stereocenters including one spiro all-carbon quaternary center, in moderate to good yields with excellent stereoselectivities (up to 15:1 dr, >99% ee). The synthetic transformations of the resulting products were also be achieved.

Original languageEnglish
Pages (from-to)1036-1039
Number of pages4
JournalOrganic Letters
Volume19
Issue number5
DOIs
Publication statusPublished - 3 Mar 2017

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Zhao, B. L., & Du, D. M. (2017). Enantioselective Squaramide-Catalyzed Trifluoromethylthiolation-Sulfur-Michael/Aldol Cascade Reaction: One-Pot Synthesis of CF3S-Containing Spiro Cyclopentanone-Thiochromanes. Organic Letters, 19(5), 1036-1039. https://doi.org/10.1021/acs.orglett.6b03846