One-pot synthesis and theoretical calculation for trifluoromethylated pyrrolizidines by 1,3-dipolar cycloaddition with azomethine ylides and β-trifluoromethyl acrylamides

被引：15
|
作者：
Toma, Yoshiki [1 ]
Kunigami, Masataka [1 ]
Watanabe, K-jiro [1 ]
Higashi, Masahiro [1 ]
Arimitsu, Satoru [1 ]
机构：
[1] Univ Ryukyus, Dept Chem Biol & Marine Sci, 1 Senbaru, Nishihara, Okinawa 9030123, Japan
来源：
JOURNAL OF FLUORINE CHEMISTRY | 2016年 / 189卷
关键词：
Trifluoromethylated pyrrolizidines; 1,3-dipolar cycloaddition; beta-Trifluoromethyl acrylamides; Diastereoselective; DFT calculation; MEDICINAL CHEMISTRY; IONIC-SOLUTIONS; PROLINE; FLUORINE; REGIOSELECTIVITY; REACTIVITY; ACCESS; DFT;
D O I：
10.1016/j.jfluchem.2016.07.013
中图分类号：
O61 [无机化学];
学科分类号：
070301 ; 081704 ;
摘要：
The reaction with beta-trifluoromethyl acrylamide 3e and azomethine ylides generated from L-proline and several aldehydes provided the corresponding trifluoromethylated pyrrolizidines with excellent diastereoselectivity (>20/1) in all cases and moderate regioselectivity (up to 1/5.9). A DFT calculation was also examined to reveal the origin of these stereoselectivities. (C) 2016 Elsevier B.V. All rights reserved.
引用
收藏
页码：22 / 32
页数：11
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