Synthesis of Boc-protected cis-and trans-4-trifluoromethyl-D-prolines

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	Synthesis of Boc-protected cis-and trans-4-trifluoromethyl-D-prolines
	Qiu XL(邱小龙) ; Qing FL(卿凤翎)
刊名	J. Chem. Soc.-Perkin Trans. 1
	2002
期号	18 页码:2052-2057
ISSN号	1472-7781
其他题名	N-Boc-cis和-trans-4-三氟甲基-D-脯氨酸的合成
通讯作者	卿凤翎
英文摘要	Both Boc-protected transand cis-4-trifluoromethyl prolines were synthesized starting from L-serine simultaneously.In our synthetic route, the key in termediate 4 was obtained through the reaction of Garner's aldehyde 1 with ylide 2 followed by trifluoromethylation with FSO^2CF^@COOM-CuI. After hydrogenationfollowed by reduction of 4, the alcohol 5 was obtained in low diastereoselectivity, however, the two diastereoisomers could be sepaated easily by flash chromatography in the following steps. The bromide 8b obtained from the alcohol 5 in a straightforwared fashion could not afford the desired cyclization product because of the strong electron-withdrawing properties of the trifluoromethyl group and the low ability of bromide as a leaving group. Instead, mesylation of alcohols 12a and 12b followed by treatment with potassium bis(trimethylsily)amide (KHMDS) afforded the desired cyclization products 13a and 13b respectively, which were transformed in to Boc-protected cis-and trans-4-trifluoromethyl-D-prolines in a straightforward fashion
学科主题	氟化学
收录类别	SCI
原文出处	http://dx.doi.org/10.1039/b206719f
语种	英语
公开日期	2013-02-22
内容类型	期刊论文
源URL	[http://202.127.28.38/handle/331003/17485]
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	Qiu XL,Qing FL. Synthesis of Boc-protected cis-and trans-4-trifluoromethyl-D-prolines[J]. J. Chem. Soc.-Perkin Trans. 1,2002(18):2052-2057.
APA	邱小龙,&卿凤翎.(2002).Synthesis of Boc-protected cis-and trans-4-trifluoromethyl-D-prolines.J. Chem. Soc.-Perkin Trans. 1(18),2052-2057.
MLA	邱小龙,et al."Synthesis of Boc-protected cis-and trans-4-trifluoromethyl-D-prolines".J. Chem. Soc.-Perkin Trans. 1 .18(2002):2052-2057.