Domino imino-aldol-aza-Michael and imino-aldol-aza-Michael-imino-aldol reactions: Diastereoselective synthesis of highly functionalized 2,6-disubstituted piperidines

被引：1

作者：

Das, Subhomoy ^{[1
,2
]}

Goswami, Gaurav ^{[1
]}

Halder, Sandipan ^{[1
,3
]}

Ghorai, Manas K. ^{[1
]}

机构：

[1] Indian Inst Technol, Dept Chem, Kanpur 208016, Uttar Pradesh, India

[2] Bar Ilan Univ, Dept Chem, IL-52900 Ramat Gan, Israel

[3] VNIT, Dept Chem, Nagpur 440010, Maharashtra, India

来源：

TETRAHEDRON | 2021年 / 93卷

关键词：

Domino; lmino-aldol-aza-Michael; lmino-aldol-aza-Michael-imino-aldol; 2,6-disubstituted piperidines; Diasteroselective; ENANTIOSELECTIVE TOTAL-SYNTHESIS; DIPHENYLPROLINOL SILYL ETHER; RING-OPENING-CYCLIZATION; FORMAL 4+2 CYCLOADDITION; ASYMMETRIC-SYNTHESIS; STEREOSELECTIVE-SYNTHESIS; SUBSTITUTED PIPERIDINES; MULTICOMPONENT REACTIONS; EFFICIENT SYNTHESIS; N-SULFONYLIMINES;

D O I：

10.1016/j.tet.2021.132285

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Enolate mediated domino imino-aldol-aza-Michael and domino imino-aldol-aza-Michael-imino-aldol reactions of alpha-(aryl/alkyl)methylidene-beta-diketones with activated N-aryl aldimines (1.0 and 2.0 equiv., respectively) have been developed for the diastereoselective (de >99%) synthesis of two sets of highly functionalized 2,6-disubstituted piperidines. The reaction course follows an intermolecular imino-aldol reaction followed by an intramolecular aza-Michael reaction with 1.0 equiv. of imine; whereas another intermolecular imino-aldol reaction takes place when 2.0 equiv. of imine is present in the reaction medium. The formation of the piperidine derivatives has been explained by plausible reaction mechanisms. (C) 2021 Elsevier Ltd. All rights reserved.

引用

页数：10

共 46 条

[1] Domino Imino-Aldol-Aza-Michael Reaction: One-Pot Diastereo- and Enantioselective Synthesis of Piperidines
Ghorai, Manas K.
Halder, Sandipan
Das, Raj Kumar
JOURNAL OF ORGANIC CHEMISTRY, 2010, 75 (21): : 7061 - 7072
[2] Tandem Michael imino-aldol reactions catalyzed by samarium diiodide
Jaber, N
Fiaud, JC
Collin, J
TETRAHEDRON LETTERS, 2001, 42 (52) : 9157 - 9159
[3] Domino Michael aldol and domino Michael Mannich reactions: highly stereoselective synthesis of functionalized cyclohexanes
Schneider, C
Reese, O
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2000, 39 (16) : 2948 - 2950
[4] Domino Michael Aldol and Domino Michael Mannich reactions: Highly stereoselective synthesis of functionalized cyclohexanes
Schneider, Christoph
Reese, Oliver
Angewandte Chemie (International Edition in English), 2000, 39 (16): : 2948 - 2950
[5] Domino Michael-Michael and Aldol-Aldol Reactions: Diastereoselective Synthesis of Functionalized Cyclohexanone Derivatives Containing Quaternary Carbon Center
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Halder, Sandipan
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JOURNAL OF ORGANIC CHEMISTRY, 2015, 80 (19): : 9700 - 9712
[6] Tandem Aza-Michael-Aldol Reactions: One-Pot Synthesis of Functionalized Piperidine Derivatives
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JOURNAL OF HETEROCYCLIC CHEMISTRY, 2014, 51 (02) : 532 - 538
[7] Synthesis of New Highly Functionalized Quinolines via a Novel Fe III -Catalyzed Domino aza-Michael/Aldol/Aromatization Reaction
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[8] Organocatalytic Asymmetric Synthesis of Functionalized 1,3,5-Triarylpyrrolidin-2-ones via an Aza-Michael/Aldol Domino Reaction
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[9] Proline-Catalyzed Diastereoselective Synthesis of Dihydroquinolinyl-Spirooxindole via Aza-Michael/Aldol Reaction
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[10] Domino Multicomponent Michael-Michael-Aldol Reactions under Phase-Transfer Catalysis: Diastereoselective Synthesis of Pentasubstituted Cyclohexanes
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