P-94 アルケンの新規付加型酸化 : アルケニルシランのオゾン酸化(ポスター発表の部)

概要

論文の詳細を見る
Ozone is one of the simplest, economical, clean and efficient oxidation agents thereby widely utilized in various fields. Also in the field of organic synthesis, ozone is quite important agent, especially for the oxidative cleavage of carbon-carbon double bond which is well recognized as a "textbook reaction". On the other hand, addition-type oxidation of alkene is also important transformation in organic synthesis, however utilization of ozone for this purpose has been severely limited. To this end, we recently found that ozone oxidation of alkenylsilane 4 provides α-silylperoxy aldehyde or ketone 5 via addition-type oxidation. Thus obtained silylperoxides 5 can serves as a versatile precursor for polyol derivatives and acyloin compounds. For example, the silylperoxy moiety of 5 can be converted to silyl ether or carbonyl group by treatment with reducing agent or base, respectively. On the other hand, nucleophilic addition reaction of carbonyl group on 5 proceeds with the preservation of peroxide moiety in good to excellent diastereoselectivity. Detailed mechanism of the oxidation, its scope and limitation together with further synthetic elaboration of silylperoxides 5 will be presented.
天然有機化合物討論会の論文
2008-09-01