Intramolecular silicon-assisted cross-coupling reactions: General synthesis of medium-sized rings containing a 1,3-cis-cis diene unit

Scott E. Denmark, Shyh Ming Yang

Research output: Contribution to journalArticlepeer-review

Abstract

The combination of ring-closing metathesis and Pd-catalyzed, silicon-assisted intramolecular cross-coupling has been developed to provide an effective and powerful method for construction of medium-sized rings with an internal 1,3-cis-cis diene unit. Allylic alcohols bearing a Z-iodoalkenyl tether can be silylated with chlorodimethylvinylsilane and subjected to Mo-catalyzed ring-closing metathesis to form unsaturated siloxanes. Activation of the siloxane with tetrabutylammonium fluoride in the presence of [allylPdCl]2 leads to high yielding ring-closing reactions to form 9-, 10-, 11- and 12-membered rings. Extension to the synthesis of 9-membered ring unsaturated ethers has also been accomplished. Noteworthy features of this process include: (1) a highly stereospecific intramolecular coupling process, (2) flexible positioning of the hydroxy group, and (3) potential extension to other medium-sized carbocycles and heterocycles.

Original languageEnglish (US)
Pages (from-to)2102-2103
Number of pages2
JournalJournal of the American Chemical Society
Volume124
Issue number10
DOIs
StatePublished - Mar 13 2002

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

Fingerprint Dive into the research topics of 'Intramolecular silicon-assisted cross-coupling reactions: General synthesis of medium-sized rings containing a 1,3-cis-cis diene unit'. Together they form a unique fingerprint.

Cite this