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Asymmetric synthesis and chiral HPLC analysis of three chiral vicinal diols
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- Author:
- No author available
- Journal Title:
- JOURNAL OF THE FOURTH MILITARY MEDICAL UNIVERSITY
- Issue:
- 10
- DOI:
- 10.3321/j.issn:1000-2790.2002.10.001
- Key Word:
- 反式二苯乙烯;萘基烯丙基醚;苯乙烯;不对称二羟基化;手性邻二醇;色谱法,高压液相中图号;O622.3
Abstract： 目的立体选择性地合成(1R, 2R)-(+)-1,2-二苯基-1,2-乙二醇(A),(S)-(+)-3-萘氧基-1,2-丙二醇(B)和(R)-(-)-1-苯基-1,2-乙二醇(C). 方法以tBuOH/H2O(1∶1)为溶剂,以K3Fe(CN)6为共氧化剂,用DHQD-PHAL-OPEG-OMe/OsO4分别催化反式二苯乙烯、萘基烯丙基醚和苯乙烯的不对称二羟基化反应. 反应结束后,通过萃取、沉淀和过滤来回收配体. 滤液减压蒸干得粗产物,进一步用柱层析分离得纯品. 产物用比旋光度法和核磁共振光谱法鉴定,其光学纯度用手性高效液相色谱法测定. 结果产物的比旋光度和1H核磁共振光谱(1H NMR)与相应二醇的化学结构相符. A, B, C的对映体过量值(enantiomer excess, ee)分别为99%,90%和82%. 结论 DHQD-PHAL-OPEG-OMe/OsO4可有效催化烯烃的不对称二羟基化反应,制备手性邻二醇. 对反式-1,2-二取代烯烃的立体选择性优于单取代烯烃.
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