Stereoselective Synthesis of Highly Substituted Conjugated Dienes via Pd-Catalyzed Carbonylation of 1,3-Diynes

Jiawang Liu, Ji Yang, Wolfgang Baumann, Ralf Jackstell, Matthias Beller

Research output: Contribution to journalArticlepeer-review

43 Scopus citations

Abstract

The stereoselective synthesis of conjugated dienes was realized for the first time via Pd-catalyzed alkoxycarbonylation of easily available 1,3-diynes. Key to success is the utilization of the specific ligand 1,1′-ferrocenediyl-bis(tert-butyl(pyridin-2-yl)phosphine) (L1), which allows this novel transformation to proceed at room temperature. A range of 1,2,3,4-tetrasubstituted conjugated dienes are obtained in this straightforward access in high yields and selectivities. The synthetic utility of the protocol is showcased in the concise synthesis of several important intermediates for construction of natural products rac-cagayanin, rac-galbulin, rac-agastinol, and cannabisin G.

Original languageEnglish
Pages (from-to)10683-10687
Number of pages5
JournalAngewandte Chemie International Edition in English
Volume58
Issue number31
DOIs
StatePublished - 29 Jul 2019
Externally publishedYes

Keywords

  • 1,3-dienes
  • P ligands
  • carbonylation
  • palladium
  • stereoselectivity

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