Regioselective and stereoselective nucleophilic ring opening of trifluoromethylated cyclic sulfates: Asymmetric synthesis of both enantiomers of syn-(3-trifluoromethyl)isoserine

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	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.
	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.