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

Subhomoy Das; Gaurav Goswami; Sandipan Halder; Manas K. Ghorai

doi:10.1016/j.tet.2021.132285

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

Subhomoy Das, Gaurav Goswami, Sandipan Halder, Manas K. Ghorai

Department of Chemistry

Research output: Contribution to journal › Article › peer-review

1 Scopus citations

Abstract

Enolate mediated domino imino-aldol-aza-Michael and domino imino-aldol-aza-Michael-imino-aldol reactions of α-(aryl/alkyl)methylidene-β-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.

Original language	English
Article number	132285
Journal	Tetrahedron
Volume	93
DOIs	https://doi.org/10.1016/j.tet.2021.132285
State	Published - 30 Jul 2021

Bibliographical note

Publisher Copyright:
© 2021 Elsevier Ltd

Funding

M.K.G. is grateful to SERB (DST) and IIT Kanpur, India, for financial support. S.D., G.G. and S.H. thank U.G.C, India, for a research fellowship.

Funders	Funder number
Indian Institute of Technology Kanpur
Department of Science and Technology, Ministry of Science and Technology, India
Science and Engineering Research Board

Keywords

2,6-disubstituted piperidines
Diasteroselective
Domino
Imino-aldol-aza-Michael
Imino-aldol-aza-Michael-imino-aldol

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10.1016/j.tet.2021.132285

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abstract = "Enolate mediated domino imino-aldol-aza-Michael and domino imino-aldol-aza-Michael-imino-aldol reactions of α-(aryl/alkyl)methylidene-β-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.",

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AU - Das, Subhomoy

AU - Goswami, Gaurav

AU - Halder, Sandipan

AU - Ghorai, Manas K.

PY - 2021/7/30

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KW - 2,6-disubstituted piperidines

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

Abstract

Bibliographical note

Funding

Keywords

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