2-Chlorotetrafluoroethanesulfinamide induced asymmetric vinylogous Mannich reaction

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	2-Chlorotetrafluoroethanesulfinamide induced asymmetric vinylogous Mannich reaction
	Liu LJ(刘丽娟); Liu JT(刘金涛)
刊名	Tetrahedron
	2014
卷号	70 期号:6 页码:1236-1245
其他题名	2-氯四氟乙基亚磺酸胺诱导的不对称vinylogous Mannich反应
通讯作者	刘金涛
英文摘要	The generality of (S)-2-chlorotetrafluoroethanesulfinamide (CTFSA) induced asymmetric vinylogous Mannich (AVM) addition reaction has been investigated. The reaction of aldimines derived from (S)-CTFSA with 2-(tert-butyldimethylsilyloxy) furan (TBSOF) took place regioselectively at the gamma-site at room temperature in DMSO under air atmosphere to give the desired addition products in syn-configuration with high diastereoselectivities (up to 98:2 dr). However, anti-configuration product as major isomer was obtained in the presence of tetra-butyl ammonium fluoride (TBAF) at -78 degrees C. Facile removal of the auxiliary group without epimerization demonstrated their synthetic potential for piperidone derivatives. (C) 2013 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.2013.12.071
语种	英语
内容类型	期刊论文
源URL	[http://ir.sioc.ac.cn/handle/331003/38833]
专题	上海有机化学研究所_中科院有机氟化学重点实验室
作者单位	中科院上海有机化学研究所
推荐引用方式 GB/T 7714	Liu LJ,Liu JT. 2-Chlorotetrafluoroethanesulfinamide induced asymmetric vinylogous Mannich reaction[J]. Tetrahedron,2014,70(6):1236-1245.
APA	刘丽娟,&刘金涛.(2014).2-Chlorotetrafluoroethanesulfinamide induced asymmetric vinylogous Mannich reaction.Tetrahedron,70(6),1236-1245.
MLA	刘丽娟,et al."2-Chlorotetrafluoroethanesulfinamide induced asymmetric vinylogous Mannich reaction".Tetrahedron 70.6(2014):1236-1245.