Reactivity of (E)-1-(tert-Butyldimethyl)silyloxy-3,3-bis(tributylstannyl)-Propene : Syn Selective SE′ Addition to Aldehydes

✍ Scribed by David Madec; Jean-Pierre Ferezou

• Book ID: 104257888
• Publisher: Elsevier Science
• Year: 1997
• Tongue: French
• Weight: 635 KB
• Volume: 38
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(97)01559-1

✦ Synopsis

Absfract: The reactivity of (a-l-(tert-bu~ldimetiyl)silyloxy-3,3-bk(tibutyls@nyl)pm~ne 1 as potendat 1,3 dianion equivalenthas been investigated.Condensationwith atdehydes4z-h, in preaenee of BF3.0Et2, afforded in high yields the mono-protected diols 5a-h exhibiting an exclusive E configurationof the vinyltinresidue. Good to high syn seleedvi!ieshave been measured,inagreement with an SE'addition meehanism. Further transformationof the resulting virrylrinmoiety of these diets into variousfunctionefitieshasbeen successfullytested. Q 1997Elsevier ScienceLtd.