Stereodivergent Synthesis of Aldol Products Using Pseudo-C2 Symmetric N-benzyl-4-(trifluoromethyl)piperidine-2,6-dione

被引：0

作者：

Yada, Rina ^{[1
]}

Kawasaki-Takasuka, Tomoko ^{[1
]}

Yamazaki, Takashi ^{[1
]}

机构：

[1] Tokyo Univ Agr & Technol, Inst Engn, Div Appl Chem, 2-24-16 Nakamachi, Koganei 1848588, Japan

来源：

MOLECULES | 2024年 / 29卷 / 21期

关键词：

trifluoromethyl; pseudo-C-2; symmetry; aldol reactions; Michael addition reactions; CATALYSIS; DESIGN; ACID;

D O I：

10.3390/molecules29215129

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

The present article describes the successful performance of crossed aldol reactions of the CF3-containing pseudo-C-2 symmetric cyclic imide with various aldehydes. The utilization of HMPA as an additive attained the preferential formation of the anti-products in good to excellent yields, which contrasts with our previous method without this additive, proceeding to furnish the corresponding syn-isomers. The effective participation of ketones and alpha,beta-unsaturated carbonyl compounds in reactions with this imide was also demonstrated to expand the application of this imide.

引用

页数：13

共 10 条

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Inoue, Yuta
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CHEMICAL COMMUNICATIONS, 2018, 54 (71) : 9913 - 9916
[2] A simple and efficient synthesis of a series of N-(thiazol-2-yl)piperidine-2,6-dione compounds and their interesting NLO properties
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[3] Synthesis and asymmetric hydrogenation of (3E)-1-benzyl-3-[(2-oxopyridin-1(2H)-yl)methylidene]piperidine-2,6-dione
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[4] Palladium-catalyzed [4+2] cycloaddition of amido-tethered allylic carbonates with oxazol-5-(4H)-ones: synthesis of piperidine-2,6-dione derivatives
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ORGANIC CHEMISTRY FRONTIERS, 2023, 10 (03) : 813 - 818
[5] METABOLISM AND PHARMACOKINETICS OF THE N-NORMAL-OCTYL AND C-NORMAL-OCTYL ANALOGS OF PYRIDOGLUTETHIMIDE [3-ETHYL-3-(4-PYRIDYL)PIPERIDINE-2,6-DIONE] - NOVEL INHIBITORS OF AROMATASE
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[6] Synthesis and study of 1,3,7-trimethylpurine-2,6-dione hydrogen dodecatungstenphosphate of composition (C8N4O2H11)2HPW12O40
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RUSSIAN JOURNAL OF GENERAL CHEMISTRY, 2009, 79 (06) : 1063 - 1066
[7] Synthesis and study of 1,3,7-trimethylpurine-2,6-dione hydrogen dodecatungstenphosphate of composition (C8N4O2H11)2HPW12O40
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[8] STUDY OF BENZO[C,D]INDOLIN-2-ONE DERIVATIVES .13. SYNTHESIS OF N,N'-DIACETYL-1,5H-INDOLINO[3,4,5-C,D,E]INDOLINE-2,6-DIONE
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[9] Synthesis and physicochemical study of di(1,3,7-trimethylpurine-2,6-dione) 12-tungstosilicate (C8N4O2H11)2H2SiW12O40
Kirichenko, O. A.
Kaziev, G. Z.
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[10] Synthesis and physicochemical study of di(1,3,7-trimethylpurine-2,6-dione) 12-tungstosilicate (C8N4O2H11)2H2SiW12O40
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G. Z. Kaziev
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Russian Journal of General Chemistry, 2012, 82 : 175 - 179

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