反应动力学拆分法合成(2S,4R)和(2S,4S)-6-庚烯-2,4-二醇

Synthesis of (2S,4R) and (2S,4S)-Hept-6-ene-2,4-diol via kinetic resolution

本研究以手性(S)-3-羟基-丁酸甲酯为原料,经TBSCl保护羟基、DIBAL-H还原及烯丙基锌试剂反应后合成(2S,4R/S)-6-庚烯-2,4-二醇中间体,利用anti/syn-1,3-二醇在进行丙酮叉保护以及脱丙酮叉保护时反应动力学性能上的差异,并通过高立体选择性的动力学拆分法合成出目标产物(2S,4S)和(2S,4R)-6-庚烯-2,4-二醇.

The chiral(S)-3-hydroxy-butyric acid methyl ester was used as raw material to synthesize(2S,4R/S)-6-heptene-2,4-diol by protection of hydroxyl groups as tert-butyldimethyl-silyl derivative,reduction with DIBAL-H and addition with allyl zinc reagent,then the target product(2S,4S)and(2S,4R)-6-heptene-2,4-diols were stereoselectively synthesized by kinetic resolution,the method relied on the different formation or hydrolysis rates of the corresponding diastereomeric acetonides.