Stereo- and Regiochemistry of Aldehyde Insertions into the C—Si Bonds of Siliranes

摘要

We have demonstrated that the aldehyde insertion reactions of siliranes proceed with stereo- and regio-chemical control, the exact course depending on reaction conditions. Furthermore, the oxasilacyclopentane products can be oxidized to afford 1,3-diols, suggesting that siliranes may be synthetic as well as reactive intermediates. With this basic knowledge of the stereo- and regiochemistry of silirane chemistry and its dependence on reaction conditions, we are exploring new reactions of siliranes in order to probe their mechanisms and applications in organic synthesis.