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A Chiral Pool and Cross Metathesis Based Synthesis of Gingerdiols
其他题名姜二醇的一种基于手性元-烯碳互换反应的合成
Wan ZL(万致力)1; Zhang GL(张国梁)1; Chen HJ(陈慧君)1; Wu YK(伍贻康)1; Li Y(李焰)1
2014
发表期刊Eur. J. Org. Chem.
卷号2014期号:10页码:2128-2139
摘要Both (3R,5S)- and (3R,5R)-gingerdiols were synthesized. Their 1,3-diol motifs were derived from enantiopure epoxy chiral building blocks that were readily accessible from D-gluconolactone. The effect of deuterating the OH groups of the natural isomer on its optical rotation was also examined. In the course of the syntheses of the targets, an unexplored cross-metathesis (CM) reaction of unprotected 5-substituted pent-1-ene-3,5-diols was investigated, in which the CM product readily underwent an allylic epimerization and oxidation, as the starting diols rearranged into ketones with unprecedented ease. These problems were eventually resolved by performing the CM reaction in toluene in the presence of phenol. The cause of these unexpected, yet very interesting phenomena, was determined to be the presence of the unprotected OH group at C-5 of the 5-substituted pent-1-ene-3,5-diol. A mechanistic rationale is also presented.
学科领域有机化学
DOI10.1002/ejoc.201301727
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收录类别SCI
语种英语
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被引频次:7[WOS]   [WOS记录]     [WOS相关记录]
文献类型期刊论文
条目标识符http://ir.sioc.ac.cn/handle/331003/38941
专题生命有机化学国家重点实验室
通讯作者Wu YK(伍贻康); Li Y(李焰)
作者单位1.湖北大学
2.中科院上海有机化学研究所
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Wan ZL,Zhang GL,Chen HJ,et al. A Chiral Pool and Cross Metathesis Based Synthesis of Gingerdiols[J]. Eur. J. Org. Chem.,2014,2014(10):2128-2139.
APA 万致力,张国梁,陈慧君,伍贻康,&李焰.(2014).A Chiral Pool and Cross Metathesis Based Synthesis of Gingerdiols.Eur. J. Org. Chem.,2014(10),2128-2139.
MLA 万致力,et al."A Chiral Pool and Cross Metathesis Based Synthesis of Gingerdiols".Eur. J. Org. Chem. 2014.10(2014):2128-2139.
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