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学科主题: 氟化学
题名: 2-Chlorotetrafluoroethanesulfinamide induced asymmetric vinylogous Mannich reaction
其他题名: 2-氯四氟乙基亚磺酸胺诱导的不对称vinylogous Mannich反应
作者: Liu LJ(刘丽娟); Liu JT(刘金涛)
通讯作者: 刘金涛
刊名: Tetrahedron
发表日期: 2014
DOI: 10.1016/j.tet.2013.12.071
卷: 70, 期:6, 页:1236-1245
收录类别: SCI
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.
语种: 英语
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内容类型: 期刊论文
URI标识: http://ir.sioc.ac.cn/handle/331003/38833
Appears in Collections:中科院有机氟化学重点实验室_期刊论文

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作者单位: 中科院上海有机化学研究所

Recommended Citation:
Liu LJ,Liu JT. 2-Chlorotetrafluoroethanesulfinamide induced asymmetric vinylogous Mannich reaction[J]. Tetrahedron,2014,70(6):1236-1245.
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