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

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	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
	Chen Q(陈琦) ; Qiu XL(邱小龙) ; Qing FL(卿凤翎)
刊名	J. Org. Chem.
	2006
卷号	71 期号:10 页码:3762-3767
ISSN号	0022-3263
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
通讯作者	卿凤翎
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.
学科主题	氟化学 ; 金属有机化学
收录类别	SCI
原文出处	http://dx.doi.org/10.1021/jo0601157
语种	英语
WOS记录号	WOS:000237417400012
公开日期	2013-02-22
内容类型	期刊论文
源URL	[http://202.127.28.38/handle/331003/17583]
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	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.
APA	陈琦,邱小龙,&卿凤翎.(2006).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. Org. Chem.,71(10),3762-3767.
MLA	陈琦,et al."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. Org. Chem. 71.10(2006):3762-3767.