A direct catalytic asymmetric aldol reaction of α-sulfanyl lactones: Efficient synthesis of SPT inhibitors

Sho Takechi, Shigeo Yasuda, Naoya Kumagai, Masakatsu Shibasaki

Research output: Contribution to journalArticlepeer-review

25 Citations (Scopus)

Abstract

Softly does it: The title reaction, catalyzed by a AgPF 6/(R)- biphep-type ligand/DBU complex, is described (see scheme). This protocol gives efficient access to syn-configured α-sulfanyl-β-hydroxy lactones in a highly enantioselective manner. In one particular case, the sulfide group was stereospecifically replaced with a hydroxy group to afford an enantioenriched tertiary alcohol, which upon further manipulation led to a class of densely functionalized SPT inhibitors.

Original languageEnglish
Pages (from-to)4218-4222
Number of pages5
JournalAngewandte Chemie - International Edition
Volume51
Issue number17
DOIs
Publication statusPublished - 2012 Apr 23
Externally publishedYes

Keywords

  • SPT inhibitor
  • aldol reaction
  • asymmetric catalysis
  • silver
  • sulfanyl lactone

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)

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