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学科主题: 氟化学 ; 生命有机化学
题名: Regioselective and stereoselective nucleophilic ring opening of trifluoromethylated cyclic sulfates: Asymmetric synthesis of both enantiomers of syn-(3-trifluoromethyl)isoserine
其他题名: 含三氟甲基的环状硫酸脂位置和立体选择性亲核开环: 不对称合成syn-(3-Trifuoromethyl)isoserine 的两个对对映体
作者: Jiang ZX(江中兴) ; Qing FL(卿凤翎)
通讯作者: 卿凤翎
刊名: J. Org. Chem.
发表日期: 2004-01-01
卷: 69, 期:16, 页:5486-5489
收录类别: SCI
部门归属: 中国科学院上海有机化学研究所元素有机化学实验室; 东华大学
英文摘要: A novel and efficient enantioselective synthesis of both enantiomers of syn-(3-trifluoromethyl)isoserine was achieved. Ring opening of trifluoromethylated cyclic sulfates 3, derived from enantiopure trifluoromethylated vicinal diols 2, with various nucleophiles occurred exclusively at C2 with inversion of chirality. Treatment of 4c and 4d, obtained by nucleophilic opening of 3a and 3b with PhCO2NH4, with (CF3SO2)(2)O followed by substitution with sodium azide, Jones oxidation, and hydrogenolysis furnished (2S,3S)-(N-benzoyl)-3-(trifluoromethyl)isoserine 9a and (2R,3R)-(N-benzoyl)-3-(trifluoromethyl)isoserine 9b, respectively.
语种: 英语
相关网址: 查看原文
WOS记录号: WOS:000223008100048
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内容类型: 期刊论文
URI标识: http://ir.sioc.ac.cn/handle/331003/17511
Appears in Collections:中科院有机氟化学重点实验室_期刊论文

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Recommended Citation:
Jiang ZX,Qing FL. Regioselective and stereoselective nucleophilic ring opening of trifluoromethylated cyclic sulfates: Asymmetric synthesis of both enantiomers of syn-(3-trifluoromethyl)isoserine[J]. J. Org. Chem.,2004,69(16):5486-5489.
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