Strained organosilacyclic compounds: synthesis of anti-Bredt olefins and trans-dioxasilacyclooctenes.
Insertions of silylenes into the allylic carbon-oxygen bond of vinyl epoxides was shown to generate 1,2-silaoxetanes. These intermediates undergo highly diastereoselective additions to aldehydes to form anti-Bredt olefins and trans-dioxasilacyclooctenes. Additions of electrophiles could be performed selectively on the outside face of these strained trans-cycloalkenes to provide valuable functionalized compounds.
Prévost
Michel
M
Department of Chemistry, University of California, Irvine, California 92697-2025, USA.
Ziller
Joseph W
JW
Woerpel
K A
KA
D000475:Alkenes / Q000138:chemical synthesis / Q000737:chemistry*; D018360:Crystallography, X-Ray; D034242:Cyclooctanes / Q000138:chemical synthesis / Q000737:chemistry*; D007536:Isomerism; D008968:Molecular Conformation; D012828:Silicones / Q000737:chemistry*
D000475:Alkenes; D034242:Cyclooctanes; D012828:Silicones