An intramolecular ring expansion of in situ formed
3-silaazetidine with internal alkynes has been developed via Pd-catalyzed
Si–C bond activation. The reaction gives rise to 6,5- and 6,6-fused
bicyclic 1,3-azasilines, in which the silicon atom locates at the
ring junction position.
A nonracemic 3-silyl-3-borylhex-4-enoate reagent has
been developed.
Its asymmetric crotylboration of aldehydes provides Z-anti-homoallylic alcohols possessing a trisubstituted
vinylsilane in high yields with excellent stereo- and enantioselectivity.
Diverse decoration of vinylsilane and ester groups, as well as formation
of functionalized THF rings, showcase the potential of the approach
in the synthesis of polyketide natural products.
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