Asymmetric Synthesis of β-Aryl β-Imido Sulfones Using Rhodium Catalysts with Chiral Diene Ligands: Synthesis of Apremilast

Jin Fong Syu, Balraj Gopula, Jia Hong Jian, Wei Sian Li, Ting Shen Kuo, Ping Yu Wu, Julian P. Henschke, Meng Chi Hsieh, Ming Kang Tsai, Hsyueh Liang Wu

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Abstract

A chiral rhodium(I)-diene catalyst enabled the one-step synthesis of β-aryl β-imido sulfones under mild reaction conditions. By selection of the chiral diene ligand L1a or L2, each enantiomer of the chiral β-aryl β-imido sulfone target can be accessed with high stereoselectivity. Demonstration of the scope of the reaction, which includes the synthesis of an N-protected chiral β-amino β-phenyl sulfone, culminated with the efficient synthesis of the heteroatom-rich active pharmaceutical ingredient apremilast.

Original languageEnglish
Pages (from-to)4614-4618
Number of pages5
JournalOrganic Letters
Volume21
Issue number12
DOIs
Publication statusPublished - 2019 Jun 21

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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    Syu, J. F., Gopula, B., Jian, J. H., Li, W. S., Kuo, T. S., Wu, P. Y., Henschke, J. P., Hsieh, M. C., Tsai, M. K., & Wu, H. L. (2019). Asymmetric Synthesis of β-Aryl β-Imido Sulfones Using Rhodium Catalysts with Chiral Diene Ligands: Synthesis of Apremilast. Organic Letters, 21(12), 4614-4618. https://doi.org/10.1021/acs.orglett.9b01513