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.
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页数：10
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