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Asymmetric synthesis of beta,beta-difluoroamino acids via cross-coupling and Strecker reactions
其他题名Asymmetric synthesis of beta,beta-difluoroamino acids via cross-coupling and Strecker reactions
Wang XJ(王小进); Zhang F(张帆); Liu JT(刘金涛)
2008
发表期刊Tetrahedron
ISSN0040-4020
卷号64期号:8页码:1731-1735
摘要beta,beta-Difluoroamino acids were synthesized from commercially available ethyl bromodifluoroacetate using cross-coupling and Strecker reactions as key steps. The coupling reaction of aryl iodides with ethyl bromodifluoroacetate gave the corresponding coupling products, which were transformed to 2-difluoromethyl-1,3-oxazolidines in two steps. Boron trifluoride etherate promoted Strecker reaction of 2-difluoromethyl-1,3-oxazoliclines gave alpha-amino nitriles in good yields and diastereoselectivities. After removal of chiral auxiliary and hydrolysis of the nitrile group, beta,beta-difluorophenylalanine was obtained with 73% ec. Partial racemization occurred during the hydrolysis of nitrile group. (C) 2007 Elsevier Ltd. All rights reserved.
学科领域氟化学
部门归属上海有机所
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收录类别SCI
语种英语
WOS记录号WOS:000253620600017
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文献类型期刊论文
条目标识符http://ir.sioc.ac.cn/handle/331003/23366
专题中科院有机氟化学重点实验室
通讯作者Liu JT(刘金涛)
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GB/T 7714
Wang XJ,Zhang F,Liu JT. Asymmetric synthesis of beta,beta-difluoroamino acids via cross-coupling and Strecker reactions[J]. Tetrahedron,2008,64(8):1731-1735.
APA 王小进,张帆,&刘金涛.(2008).Asymmetric synthesis of beta,beta-difluoroamino acids via cross-coupling and Strecker reactions.Tetrahedron,64(8),1731-1735.
MLA 王小进,et al."Asymmetric synthesis of beta,beta-difluoroamino acids via cross-coupling and Strecker reactions".Tetrahedron 64.8(2008):1731-1735.
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