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

Research output: Contribution to journalArticlepeer-review

2 Citations (Scopus)

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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