Concise enantioselective synthesis of δ,δ-disubstituted δ-valerolactones

Akira Saito, Naoya Kumagai, Masakatsu Shibasaki

Research output: Contribution to journalArticlepeer-review

10 Citations (Scopus)

Abstract

Efficient access to enantioenriched δ,δ-disubstituted δ-valerolactones is described. A soft Lewis acid/hard Brønsted base cooperative catalyst allowed for direct catalytic asymmetric γ-addition of allyl cyanide to ketones, producing tertiary homoallylic alcohols with a Z-configured α,β-unsaturated nitrile. Electrophilic activation of the nitrile functionality triggered 6-exo-dig cyclization, and subsequent N-acylation gave rise to the δ-valerolactone skeleton via CN bond cleavage.

Original languageEnglish
Pages (from-to)3167-3171
Number of pages5
JournalTetrahedron Letters
Volume55
Issue number20
DOIs
Publication statusPublished - 2014 May 14
Externally publishedYes

Keywords

  • Cyclization
  • Nitrile
  • Silver
  • Valerolactone

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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