Selective oxidation of benzylic, allylic and propargylic alcohols using dirhodium(II) tetraamidinate as catalyst and aqueous<i>tert</i>-butyl hydroperoxide as oxidant
The reaction of trialkylvinylborates with aldehydes as applied to syntheses of 1,3-alkanediols, 1-chloro-3-heptanol and a cyclopropane derivative
作者:K. Utimoto、K. Uchida、H. Nozaki
DOI:10.1016/0040-4020(77)80382-7
日期:1977.1
R2BCHR-CH2-CH(OLi)R' (2) or its borate form (3). Oxidation of the adducts with alkaline hydrogen peroxide gives ca. 1:1 mixture of diastereomeric 1,3-alkanediols in good yields. On the other hand, the reaction of BrMg[R3BCHCH2] with R'CHO affords less satisfactory results. Successive treatment of 2 (R = n-Bu, R' = H) with PCl5 and alkaline H2O2 gives HOCHBu-CH2-CH2Cl (6). Treatment of Et2BCHEt-CH2-CHCl-Ph
THE REACTION OF LITHIUM TRIALKYLVINYLBORATES AND ALDEHYDES AS APPLIED TO THE SYNTHESIS OF 1,3-DIOLS, γ-CHLOROALCOHOL, AND CYCLOPROPANE
作者:Kiitiro Utimoto、Keiichiro Uchida、Hitosi Nozaki
DOI:10.1246/cl.1974.1493
日期:1974.12.5
Reaction of lithium trialkylvinylborates with aldehydes gives non-isolable boron compounds, 1,2-oxaborolane-bases borates (II) whose oxidative work-up furnishes 1,3-diols (III) smoothly. Successive treatment of a cyclic borate with phosphorus pentachloride and aqueous alkali provides a cyclopropane.