Reactions of Chiral Allylic Stannanes

Intra-molecular allylations are documented, as shown by the cyclization of enantioenriched stannane 273 to yield the 14-membered carbocycle 274. Constraints of the carbon tether may determine a preferred transition state geometry to minimize ring strain, delivering the Z-alkene. 

Chiral non-racemic y-[alkoxy]allylic stannanes, such as 275, react with simple aldehydes to yield vyn-l,2-diol derivative 276 in high enantiomeric excess. The anti-SE arrangement in 277 minimizes electronic and steric interactions. 

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Scheme 5.2.56 Examples of reactions involving transmetalations with InCIs 5.2.12 Reactions of Chiral Allylic Stannanes...

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