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

页码：22 / 32

页数：11

共 53 条

[1] [Anonymous], NATURALLY OCCURRING
[2] A theoretical study on the regioselectivity of 1,3-dipolar cycloadditions using DFT-based reactivity indexes
Aurell, MJ
Domingo, LR
Pérez, P
Contreras, R
[J]. TETRAHEDRON, 2004, 60 (50) : 11503 - 11509
[3] Recent advances (1995-2005) in fluorinated pharmaceuticals based on natural products
Begue, Jean-Pierre
Bonnet-Delpon, Daniele
[J]. JOURNAL OF FLUORINE CHEMISTRY, 2006, 127 (08) : 992 - 1012
[4] Highly selective 1,3-dipolar cycloaddition of a cyclic azomethine ylide to ethyltrifluorocrotonates
Bégué, JP
Bonnet-Delpon, D
Chennoufi, A
Ourévitch, M
Ravikumar, KS
Rock, MH
[J]. JOURNAL OF FLUORINE CHEMISTRY, 2001, 107 (02) : 275 - 279
[5] Understanding the regio- and chemoselective polar [3+2] cycloaddition of the Padwa carbonyl ylides with α-methylene ketones. A DFT study
Benchouk, Wafaa
Mekelleche, Sidi Mohamed
Jose Aurell, Maria
Ramon Domingo, Luis
[J]. TETRAHEDRON, 2009, 65 (24) : 4644 - 4651
[6] Recent advances in the synthesis of naturally occurring pyrrolidines, pyrrolizidines and indolizidine alkaloids using proline as a unique chiral synthon
Bhat, Chinmay
Tilve, Santosh G.
[J]. RSC ADVANCES, 2014, 4 (11) : 5405 - 5452
[7] New applications of integral equations methods for solvation continuum models: ionic solutions and liquid crystals
Cances, E
Mennucci, B
[J]. JOURNAL OF MATHEMATICAL CHEMISTRY, 1998, 23 (3-4) : 309 - 326
[8] A new integral equation formalism for the polarizable continuum model: Theoretical background and applications to isotropic and anisotropic dielectrics
Cances, E
Mennucci, B
Tomasi, J
[J]. JOURNAL OF CHEMICAL PHYSICS, 1997, 107 (08) : 3032 - 3041
[9] Synthesis of spiropyrrolidines and spiropyrrolizidines by 1,3-dipolar cycloadditions of azomethine ylides to substituted α-methylene-γ-lactones
Castulík, J
Marek, J
Mazal, C
[J]. TETRAHEDRON, 2001, 57 (39) : 8339 - 8347
[10] Intramolecular dipolar cycloaddition reactions of azomethine ylides
Coldham, I
Hufton, R
[J]. CHEMICAL REVIEWS, 2005, 105 (07) : 2765 - 2809

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