Stereoselective reduction of 1-benzyl-3,3-dimethyl-5-methylenepyrrolidine-2,4-dione using sodium borohydride with selected metal chlorides
1-benzyl-3,3-dimethyl-5-methylenepyrrolidine-2,4-dione is an intermediate product produced in the synthesis towards the natural bioactive compound, zopfiellamide A. This compound was synthesized via four main steps including dimethylations, addition with CuBr2, cyclization with benzylamine and react...
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Universiti Kebangsaan Malaysia (UKM)
2017
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| Online Access: | http://irep.iium.edu.my/60337/ http://irep.iium.edu.my/60337/1/NorSaliyana_21_5_22-2.pdf http://irep.iium.edu.my/60337/3/60337_Stereoselective%20reduction_scopus.pdf |
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| author | Jumali, Nor Saliyana Shaameri, Zurina Mohamad, Hafsah Hamzah, Ahmad Sazali |
| author_facet | Jumali, Nor Saliyana Shaameri, Zurina Mohamad, Hafsah Hamzah, Ahmad Sazali |
| author_sort | Jumali, Nor Saliyana |
| building | IIUM Repository |
| collection | Online Access |
| description | 1-benzyl-3,3-dimethyl-5-methylenepyrrolidine-2,4-dione is an intermediate product produced in the synthesis towards the natural bioactive compound, zopfiellamide A. This compound was synthesized via four main steps including dimethylations, addition with CuBr2, cyclization with benzylamine and reaction with formaldehyde. The corresponding intermediate was an α,ß-unsaturated ketone having exo-alkene group, and it was subjected to reduction using sodium borohydride and selected metal chlorides. In this study, the effect and the hydride transfer mechanism of sodium borohydride-metal chlorides system in the reduction of 1-benzyl-3,3-dimethyl-5-methylenepyrrolidine-2,4-dione was investigated based on the stereochemical outcome of the product.
Keywords: stereoselective, reduction, metal borohydride, exo-alkene |
| first_indexed | 2025-11-14T16:53:42Z |
| format | Article |
| id | iium-60337 |
| institution | International Islamic University Malaysia |
| institution_category | Local University |
| language | English English |
| last_indexed | 2025-11-14T16:53:42Z |
| publishDate | 2017 |
| publisher | Universiti Kebangsaan Malaysia (UKM) |
| recordtype | eprints |
| repository_type | Digital Repository |
| spelling | iium-603372017-12-26T03:08:28Z http://irep.iium.edu.my/60337/ Stereoselective reduction of 1-benzyl-3,3-dimethyl-5-methylenepyrrolidine-2,4-dione using sodium borohydride with selected metal chlorides Jumali, Nor Saliyana Shaameri, Zurina Mohamad, Hafsah Hamzah, Ahmad Sazali QD Chemistry 1-benzyl-3,3-dimethyl-5-methylenepyrrolidine-2,4-dione is an intermediate product produced in the synthesis towards the natural bioactive compound, zopfiellamide A. This compound was synthesized via four main steps including dimethylations, addition with CuBr2, cyclization with benzylamine and reaction with formaldehyde. The corresponding intermediate was an α,ß-unsaturated ketone having exo-alkene group, and it was subjected to reduction using sodium borohydride and selected metal chlorides. In this study, the effect and the hydride transfer mechanism of sodium borohydride-metal chlorides system in the reduction of 1-benzyl-3,3-dimethyl-5-methylenepyrrolidine-2,4-dione was investigated based on the stereochemical outcome of the product. Keywords: stereoselective, reduction, metal borohydride, exo-alkene Universiti Kebangsaan Malaysia (UKM) 2017-10 Article PeerReviewed application/pdf en http://irep.iium.edu.my/60337/1/NorSaliyana_21_5_22-2.pdf application/pdf en http://irep.iium.edu.my/60337/3/60337_Stereoselective%20reduction_scopus.pdf Jumali, Nor Saliyana and Shaameri, Zurina and Mohamad, Hafsah and Hamzah, Ahmad Sazali (2017) Stereoselective reduction of 1-benzyl-3,3-dimethyl-5-methylenepyrrolidine-2,4-dione using sodium borohydride with selected metal chlorides. Malaysian Journal of Analytical Sciences, 21 (5). pp. 1176-1182. ISSN 1394-2506 |
| spellingShingle | QD Chemistry Jumali, Nor Saliyana Shaameri, Zurina Mohamad, Hafsah Hamzah, Ahmad Sazali Stereoselective reduction of 1-benzyl-3,3-dimethyl-5-methylenepyrrolidine-2,4-dione using sodium borohydride with selected metal chlorides |
| title | Stereoselective reduction of 1-benzyl-3,3-dimethyl-5-methylenepyrrolidine-2,4-dione using sodium borohydride with selected metal chlorides |
| title_full | Stereoselective reduction of 1-benzyl-3,3-dimethyl-5-methylenepyrrolidine-2,4-dione using sodium borohydride with selected metal chlorides |
| title_fullStr | Stereoselective reduction of 1-benzyl-3,3-dimethyl-5-methylenepyrrolidine-2,4-dione using sodium borohydride with selected metal chlorides |
| title_full_unstemmed | Stereoselective reduction of 1-benzyl-3,3-dimethyl-5-methylenepyrrolidine-2,4-dione using sodium borohydride with selected metal chlorides |
| title_short | Stereoselective reduction of 1-benzyl-3,3-dimethyl-5-methylenepyrrolidine-2,4-dione using sodium borohydride with selected metal chlorides |
| title_sort | stereoselective reduction of 1-benzyl-3,3-dimethyl-5-methylenepyrrolidine-2,4-dione using sodium borohydride with selected metal chlorides |
| topic | QD Chemistry |
| url | http://irep.iium.edu.my/60337/ http://irep.iium.edu.my/60337/1/NorSaliyana_21_5_22-2.pdf http://irep.iium.edu.my/60337/3/60337_Stereoselective%20reduction_scopus.pdf |