Aldol reaction of 4-trimethylsiloxy-6-methylene-1,3-dioxines with chiral aldehydes: Enantioselective synthesis of 1,3-dioxin-4-ones having a 2,3-dihydroxylated alkyl group at the 6-position
作者:Masayuki Sato、Yoshiaki Sugita、Yumi Abiko、Chikara Kaneko
DOI:10.1016/s0957-4166(00)82101-1
日期:1992.9
A novel enantioselective synthesis of 1,3-dioxin-4-ones having a 2,3-dihydroxylated alkyl group at the 6-position has been accomplished by titanium tetrachloride-mediated aldol condensation of silyl enol ethers derived from the 6-alkylated dioxinones with chiral 2-benzyloxypropanal. The keto group of the corresponding β-keto esters obtained after cleavage of the acetal function affords, by 1,3-syn
通过四氯化钛介导的由6-烷基化二恶英酮衍生的甲硅烷基烯醇醚的醇醛缩醛的缩合反应,完成了在6-位具有2,3-二羟基化烷基的1,3-二恶英-4-酮的新型对映选择性合成。手性2-苄氧基丙醛。缩醛功能裂解后获得的相应β-酮酯的酮基通过1,3-顺和/或-抗还原,以高度对映选择性的方式提供3,5,6-三羟基庚酸。