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

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 enanti...

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Published inOrganic letters Vol. 19; no. 5; pp. 1036 - 1039
Main Authors Zhao, Bo-Liang, Du, Da-Ming
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 03.03.2017
Amer Chemical Soc
Subjects
chemical reactions
chemical structure
Chemistry
Chemistry, Organic
enantioselectivity
Lewis acids
organic compounds
Physical Sciences
Science & Technology
synthesis
HYPERVALENT IODINE REAGENT
ALDOL REACTIONS
ASYMMETRIC ORGANOCATALYSIS
DOMINO REACTIONS
BETA-KETOESTERS
STRATEGIES
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Summary: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.
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ISSN:1523-7060
1523-7052
1523-7052
DOI:10.1021/acs.orglett.6b03846