Stereo‐ and Chemoselective Enrichment of sp<sup>3</sup> Character in Post‐Ugi Morpholines

Abstract We conducted a systematic study on synthesis and modification of morpholine core using Ugi adducts derived from propiolic acid and glycolaldehyde dimer. The assembly step involved triphenylphosphine‐promoted 6‐exo‐dig umpolung oxa‐Michael cyclization of Ugi‐derived hydroxypropargylamides yielding 2‐methylenemorpholin‐3‐one derivatives. Subsequent heterogeneous catalytic hydrogenation of the exocyclic double bond proceeded in a highly diastereoselective fashion establishing a relative cis configuration in the resulting sp 3 ‐enriched morpholinone scaffold. Finally, chemoselective amide reduction with lithium aluminum hydride (LAH) allowed to obtain fully saturated morpholines while leaving the more sterically hindered exocyclic amide moiety intact. Taken together these findings outline the strategy for controlled reduction of the inherent rigidity of post‐Ugi scaffolds.

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Publication Details

Journal
European Journal of Organic Chemistry
Published
2024-11-28
DOI
https://doi.org/10.1002/ejoc.202401124
Citations
3
Primary Topic
Synthesis of Organic Compounds
Type
article
Field-Weighted Citation Impact
1.34

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article

Stereo‐ and Chemoselective Enrichment of sp3 Character in Post‐Ugi Morpholines

Olga P. Pereshivko, Niyaz Amire, Muhammad Hasan, Shun‐Yi Wang et al.
3 citations
European Journal of Organic Chemistry
Synthesis of Organic Compounds
1.34
article

Stereo‐ and Chemoselective Enrichment of sp3 Character in Post‐Ugi Morpholines

Olga P. Pereshivko, Niyaz Amire, Muhammad Hasan, Shun‐Yi Wang, Sofia D. Martynova, Manzoor Zaman, Andrey Belyaev, Azat Makhmet, Vsevolod A. Peshkov, Jiafeng Yu, Chang‐Keun Lim, Anatoly A. Peshkov, Azamat Begenov, Jing Gong, Gulzat A. Nuroldayeva, Ainara Bekbolatova
article en
3 citations

Abstract

Abstract We conducted a systematic study on synthesis and modification of morpholine core using Ugi adducts derived from propiolic acid and glycolaldehyde dimer. The assembly step involved triphenylphosphine‐promoted 6‐exo‐dig umpolung oxa‐Michael cyclization of Ugi‐derived hydroxypropargylamides yielding 2‐methylenemorpholin‐3‐one derivatives. Subsequent heterogeneous catalytic hydrogenation of the exocyclic double bond proceeded in a highly diastereoselective fashion establishing a relative cis configuration in the resulting sp 3 ‐enriched morpholinone scaffold. Finally, chemoselective amide reduction with lithium aluminum hydride (LAH) allowed to obtain fully saturated morpholines while leaving the more sterically hindered exocyclic amide moiety intact. Taken together these findings outline the strategy for controlled reduction of the inherent rigidity of post‐Ugi scaffolds.

European Journal of Organic ChemistryVol. 28(4)
L. N. Gumilyov Eurasian National University (KZ), University of Eastern Finland (FI), Soochow University (TW), Soochow University (CN), Finland University (FI), Nazarbayev University (KZ)
National Natural Science Foundation of China, China Scholarship Council, Soochow University, Priority Academic Program Development of Jiangsu Higher Education Institutions, Nazarbayev University
Clean water and sanitation
Openalex Percentile: Top 18%
Synthesis of Organic Compounds
1.34
DOIOpen Access PDFOpenAlex
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