BIOMAT Database Logo BIOMAT Database Logo

A relay ring-closing metathesis synthesis of dihydrooxasilines, precursors of (Z)-iodo olefins. 2008

Qiuzhe Xie, and Richard W Denton, and Kathlyn A Parker
Department of Chemistry, SUNY Stony Brook, Stony Brook, New York 11794-3400, USA.

A convenient Grubbs II metathesis provides dihydrooxasilines by relay RCM (RRCM). Dihydrooxasilines undergo ring opening to give Z-vinyl silanes. These can then be converted to Z-vinyl iodides. This sequence provides a short, high yield, and convenient route to trisubstituted Z-vinyl iodides, useful intermediates for the preparation of polypropionate antibiotics.

UI MeSH Term Description Entries
D007455 Iodine A nonmetallic element of the halogen group that is represented by the atomic symbol I, atomic number 53, and atomic weight of 126.90. It is a nutritionally essential element, especially important in thyroid hormone synthesis. In solution, it has anti-infective properties and is used topically. Iodine-127,Iodine 127
D002384 Catalysis The facilitation of a chemical reaction by material (catalyst) that is not consumed by the reaction. Catalyses
D000475 Alkenes Unsaturated hydrocarbons of the type Cn-H2n, indicated by the suffix -ene. (Grant & Hackh's Chemical Dictionary, 5th ed, p408) Alkene,Olefin,Olefins,Pentene,Pentenes
D012821 Silanes Compounds similar to hydrocarbons in which a tetravalent silicon atom replaces the carbon atom. They are very reactive, ignite in air, and form useful derivatives. Silane
D013237 Stereoisomerism The phenomenon whereby compounds whose molecules have the same number and kind of atoms and the same atomic arrangement, but differ in their spatial relationships. (From McGraw-Hill Dictionary of Scientific and Technical Terms, 5th ed) Molecular Stereochemistry,Stereoisomers,Stereochemistry, Molecular,Stereoisomer

Related Publications

Qiuzhe Xie, and Richard W Denton, and Kathlyn A Parker
Natural products and ring-closing metathesis: synthesis of sterically congested olefins.
January 2018, Natural product reports,
Qiuzhe Xie, and Richard W Denton, and Kathlyn A Parker
Synthesis of heterocyclic and carbocyclic fluoro-olefins by ring-closing metathesis.
September 2003, Organic letters,
Qiuzhe Xie, and Richard W Denton, and Kathlyn A Parker
Diastereoselective synthesis of trisubstituted olefins using a silicon-tether ring-closing metathesis strategy.
March 2020, Organic & biomolecular chemistry,
Qiuzhe Xie, and Richard W Denton, and Kathlyn A Parker
A formal synthesis of (-)-englerin A by relay ring closing metathesis and transannular etherification.
June 2012, Organic letters,
Qiuzhe Xie, and Richard W Denton, and Kathlyn A Parker
Ruthenium-catalyzed ring-closing metathesis to form tetrasubstituted olefins.
March 2007, Organic letters,
Qiuzhe Xie, and Richard W Denton, and Kathlyn A Parker
Total synthesis of peloruside A through kinetic lactonization and relay ring-closing metathesis cyclization reactions.
August 2010, Angewandte Chemie (International ed. in English),
Qiuzhe Xie, and Richard W Denton, and Kathlyn A Parker
Relay ring-closing metathesis-a strategy for achieving reactivity and selectivity in metathesis chemistry.
March 2005, Angewandte Chemie (International ed. in English),
Qiuzhe Xie, and Richard W Denton, and Kathlyn A Parker
Synthesis of Cembranoid Analogues through Ring-Closing Metathesis of Terpenoid Precursors: A Challenge Regarding Ring-Size Selectivity.
August 2015, Chemistry (Weinheim an der Bergstrasse, Germany),
Qiuzhe Xie, and Richard W Denton, and Kathlyn A Parker
Total synthesis of the salicylate enamide macrolide oximidine III: application of relay ring-closing metathesis.
July 2004, Angewandte Chemie (International ed. in English),
Qiuzhe Xie, and Richard W Denton, and Kathlyn A Parker
Relay ring-closing metathesis (RRCM): a strategy for directing metal movement throughout olefin metathesis sequences.
August 2004, Journal of the American Chemical Society,
Copied contents to your clipboard!