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 language | English (US) |
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Pages (from-to) | 2102-2103 |
Number of pages | 2 |
Journal | Journal of the American Chemical Society |
Volume | 124 |
Issue number | 10 |
DOIs | |
State | Published - Mar 13 2002 |
ASJC Scopus subject areas
- Catalysis
- General Chemistry
- Biochemistry
- Colloid and Surface Chemistry