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Stereoselective synthesis of allylsilanes from chloromethylsilylalkynes

โœ Scribed by Hiroshi Shiragami; Takuo Kawamoto; Kiitiro Utimoto; Hitosi Nozaki


Publisher
Elsevier Science
Year
1986
Tongue
French
Weight
228 KB
Volume
27
Category
Article
ISSN
0040-4039

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Cross-coupling reactions of various organocopper reagents with u-(mesyloxy)ailyls~lanes have been evaluated for stereoselectlve P,P-dlsubstltuted vinylsilane synthesis $2' displacements with RMgBdCuCN(cat ) reagents proceeded In high yields (84+94%) and E-selectlvltles (10 1 -+ 38 1) in THF at -78ยฐC

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The ester-allylsilanes ( 5) and ( 6) and the acid-allylsilane (7) react stereoselectively with m-CPBA; the major product from ( 5) and ( 7) was the y-lactone (4), whereas (6) failed to undergo lactonisation, the major product in this case was the P,wpoxy-silane (12).