Catalytic enantioselective carboannulation with allylsilanes

Nicolas R. Ball-Jones, Joseph J. Badillo, Ngon T. Tran, Annaliese K. Franz

Research output: Contribution to journalArticlepeer-review

44 Scopus citations

Abstract

The first catalytic asymmetric carboannulation with allylsilanes is presented. The enantioselective [3+2] annulation is catalyzed using a scandium(III)/indapybox complex with tetrakis-[3,5-bis(trifluoromethyl)phenyl]- borate (BArF) to enhance catalytic activity and control stereoselectivity. Functionalized cyclopentanes containing a quaternary carbon center are derived from alkylidene oxindole, coumarin, and malonate substrates with high stereoselectivity. The enantioselective 1,4-conjugate addition and enantioselective lactone formation (by trapping of the β-silyl carbocation) is also described. It's a trap: The catalytic asymmetric carboannulation of alkylidene oxindole, coumarin, and malonate substrates with allylsilanes in the presence of a ScIII/BArF/indapybox catalyst affords functionalized cyclopentanes containing a quaternary carbon center with high stereoselectivity. Enantioselective allylation and asymmetric lactone formation by trapping of the β-silyl carbocation are also presented.

Original languageEnglish (US)
Pages (from-to)9462-9465
Number of pages4
JournalAngewandte Chemie - International Edition
Volume53
Issue number36
DOIs
StatePublished - 2014

Keywords

  • allylic compounds
  • asymmetric catalysis
  • conjugate addition
  • cyclization
  • scandium

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