2-Chlorotetrafluoroethanesulfinamide induced asymmetric vinylogous Mannich reaction

被引：17
作者：
Liu, Li-Juan [1 ]
Liu, Jin-Tao [1 ]
机构：
[1] Chinese Acad Sci, Shanghai Inst Organ Chem, Key Lab Organofluorine Chem, Shanghai 200032, Peoples R China
来源：
TETRAHEDRON | 2014年 / 70卷 / 06期
基金：
中国国家自然科学基金;
关键词：
2-Chlorotetrafluoroethanesulfinamide; Vinylogous Mannich reaction; Chiral auxiliary; Asymmetric synthesis; PHOSPHINE-OXAZOLINE LIGANDS; ALDOL REACTION; ALDIMINES; PYRROLE; FURAN;
D O I：
10.1016/j.tet.2013.12.071
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
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.
引用
收藏
页码：1236 / 1245
页数：10
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