Asymmetric synthesis of beta,beta-difluoroamino acids via cross-coupling and Strecker reactions

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	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)
刊名	Tetrahedron
	2008
卷号	64 期号:8 页码:1731-1735
ISSN号	0040-4020
其他题名	Asymmetric synthesis of beta,beta-difluoroamino acids via cross-coupling and Strecker reactions
通讯作者	刘金涛
英文摘要	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.
学科主题	氟化学
收录类别	SCI
原文出处	http://dx.doi.org/10.1016/j.tet.2007.12.002
语种	英语
WOS记录号	WOS:000253620600017
公开日期	2013-03-11
内容类型	期刊论文
源URL	[http://202.127.28.38/handle/331003/23366]
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	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.