Flow Synthesis of (3R)- and (3S)-(E)-1-Iodohexa-1,5-dien-3-ol: Chiral Building Blocks for Natural Product Synthesis
Flow Synthesis of (3R)- and (3S)-(E)-1-Iodohexa-1,5-dien-3-ol: Chiral Building Blocks for Natural Product Synthesis
复制标题
(3R)-和(3S)-(E)-1-Iodohexa-1,5-dien-3-ol的流动合成：用于天然产物合成的手性结构单元
作者：
Sota Katayama;Tomoyuki Koge;Satoko Katsuragi;S. Akai;T. Oishi
开发了制备光学活性 (3R)-和 (3S)-(E)-1-iodohexa-1,5-dien-3-ol 的简明程序。 (E)-3-碘代丙烯酸乙酯在流动和间歇条件下通过连续半还原和格氏反应转化为外消旋(E)-1-碘六-1,5-二烯-3-醇。通过使用装在柱中的脂肪酶在流动条件下实现外消旋醇的动力学拆分，得到(3S)-(E)-1-碘六-1,5-二烯-3-醇和相应的(3R)-乙酸酯。乙酰基的去除也在流动条件下通过使用填充在柱中的离子交换树脂进行，并且在简单蒸发洗脱液后得到(3R)-(E)-1-碘六-1,5-二烯-3-醇。
A concise procedure to prepare optically active (3R)- and (3S)-(E)-1-iodohexa-1,5-dien-3-ol was developed. Ethyl (E)-3-iodoacrylate was converted to racemic (E)-1-iodohexa-1,5-dien-3-ol under flow and batch conditions via successive half reduction followed by Grignard reaction. Kinetic resolution of the racemic alcohol was achieved under flow conditions by using lipase packed in a column to afford (3S)-(E)-1-iodohexa-1,5-dien-3-ol and corresponding (3R)-acetate. Removal of the acetyl group was also carried out under flow conditions by using ion exchange resin packed in a column and (3R)-(E)-1-iodohexa-1,5-dien-3-ol was obtained after simple evaporation of the eluent.
影响因子：
15
作者：
Trost, BM;Frederiksen, MU;Shireman, BT
通讯作者：
Shireman, BT