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学科主题: 氟化学 ; 金属有机化学
题名: Indium-mediated diastereoselective allylation of D- and L-glyceraldimines with 4-bromo-1,1,1-trifluoro-2-butene: Highly stereoselective synthesis of 4,4,4-trifluoroisoleucines and 4,4,4-trifluorovaline
其他题名: 铟引发的4-溴-1,1,1-三氟-2-丁烯对D-和L-Glyceraldimines非对映选择烯丙基化反应:高立体选择性合成4,4,4-三氟异亮氨酸和4,4,4-三氟缬氨酸
作者: Chen Q(陈琦) ; Qiu XL(邱小龙) ; Qing FL(卿凤翎)
通讯作者: 卿凤翎
刊名: J. Org. Chem.
发表日期: 2006
卷: 71, 期:10, 页:3762-3767
收录类别: SCI
部门归属: 中科院上海有机化学研究所; 东华大学
英文摘要: A practical and efficient route for the stereoselective synthesis of (2R,3S)- and (2S,3R)-4,4,4-trifluoroisoleucines and (2R,3S)-4,4,4-trifluorovaline was developed. Indium-mediated allylation of (R)-N-benzyl-2,3-O-isopropylideneglyceraldimine 7 with 4-bromo-1,1,1-trifluoro-2-butene 4 gave the desired homoallylic amine 8 in high diastereoselectivity (> 95% de) with moderate yield. The Cbz-protected (2R,3S)-4,4,4-trifluoroisoleucine 14 and Boc-protected (2R,3S)-4,4,4-trifluorovaline 21 were then readily prepared from 8. In addition, following the same procedure, Cbz-protected (2S,3R)-4,4,4-trifluoroisoleucine 28, the enantiomer of 14, was prepared starting from (S)-N-benzyl-2,3-O-isopropylideneglyceraldimine 24.
语种: 英语
相关网址: 查看原文
WOS记录号: WOS:000237417400012
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内容类型: 期刊论文
URI标识: http://ir.sioc.ac.cn/handle/331003/17583
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:
Chen Q,Qiu XL,Qing FL. Indium-mediated diastereoselective allylation of D- and L-glyceraldimines with 4-bromo-1,1,1-trifluoro-2-butene: Highly stereoselective synthesis of 4,4,4-trifluoroisoleucines and 4,4,4-trifluorovaline[J]. J. Org. Chem.,2006,71(10):3762-3767.
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