Regioselective and stereoselective nucleophilic ring opening of trifluoromethylated cyclic sulfates: Asymmetric synthesis of both enantiomers of syn-(3-trifluoromethyl)isoserine | |
Jiang ZX(江中兴) ; Qing FL(卿凤翎) | |
刊名 | J. Org. Chem.
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2004 | |
卷号 | 69期号:16页码:5486-5489 |
ISSN号 | 0022-3263 |
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 |
通讯作者 | 卿凤翎 |
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. |
学科主题 | 氟化学 ; 生命有机化学 |
收录类别 | SCI |
原文出处 | http://dx.doi.org/10.1021/jo0497611 |
语种 | 英语 |
WOS记录号 | WOS:000223008100048 |
公开日期 | 2013-02-22 |
内容类型 | 期刊论文 |
源URL | [http://202.127.28.38/handle/331003/17511] ![]() |
专题 | 上海有机化学研究所_中科院有机氟化学重点实验室 |
推荐引用方式 GB/T 7714 | 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. |
APA | 江中兴,&卿凤翎.(2004).Regioselective and stereoselective nucleophilic ring opening of trifluoromethylated cyclic sulfates: Asymmetric synthesis of both enantiomers of syn-(3-trifluoromethyl)isoserine.J. Org. Chem.,69(16),5486-5489. |
MLA | 江中兴,et al."Regioselective and stereoselective nucleophilic ring opening of trifluoromethylated cyclic sulfates: Asymmetric synthesis of both enantiomers of syn-(3-trifluoromethyl)isoserine".J. Org. Chem. 69.16(2004):5486-5489. |
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