Synthesis of silacycloalkenes and silaspirenes by Ru(II)-catalyzed ring-closing metathesis reactions

Temporary Silicon‐Tethered Ring‐Closing Metathesis: Recent Advances in Methodology Development and Natural Product Synthesis

“…In a related study, Undheim and coworkers reported the synthesis of silacycloalkenes and silaspirenes from an Ru-catalyzed RCM reaction. [77] Landais and co-workers published a series of reports on the preparation and functionalization of silacyclopent-3-enes. [78] These attractive synthons, often used used as polymer precursors, have not found an extensive application in organic synthesis due to problems associated with its functionalization.…”

“…The cyclization feasibility of silaalkadienes was investigated based on the different substitution patterns and ring sizes. In a related study, Undheim and co‐workers reported the synthesis of silacycloalkenes and silaspirenes from an Ru‐catalyzed RCM reaction 77. Landais and co‐workers published a series of reports on the preparation and functionalization of silacyclopent‐3‐enes 78.…”

Allylsilanes in Organic Synthesis − Recent Developments

“…Therefore, RCM of diene 241 led to silacyclohex-3-ene 242 and not to the corresponding five-membered ring (Scheme 64). [19b,19c] Undheim [113] has shown that allylsilanes also react as the olefinic partner in enyne metathesis as illustrated by RCM of the tris(propargylic) silane 243, which afforded, under rather drastic conditions, the diene 244 in moderate yield. Finally, the same authors have reported a few examples of silaspirenes obtained by RCM of the corresponding diallylsilacycles.…”

“…Finally, the same authors have reported a few examples of silaspirenes obtained by RCM of the corresponding diallylsilacycles. [113] Scheme 64…”

“…Recently, several reports have emphasized RCM of dienes in which one of the olefins is an allylsilane. [12,19,113,114] Roush has devised an elegant route to cyclopentenes and cyclohexenes possessing an allylsilane moiety using RCM of suitable dienes. [12b,12c] The diene precursors (e.g.…”