Silacycles as templates for acyclic diastereoselection

Article abstract of DOI:10.1016/S0040-4039(98)02200-X

The 4-substituted silacyclohex-3-enes (3) prepared from the vinyl triflate (9) derived from 1,1-dimethyl-1-silacyclohexan-4-one (1) and higher- order organocuprates provides a versatile template for the construction of non-racemic 3-methyl-4-penten-1-ol (6). Through asymmetric hydroboration, 3 affords the requisite β-hydroxysilane (4) with the idea/geometry to undergo elimination to the chiral acyclic silane (5) which is oxidatively converted to 6.