Stereoselective reduction of 1-benzyl-3,3-dimethyl-5-methylenepyrrolidine-2,4-dione using sodium borohydride with selected metal chlorides; [Tindak balas penurunan stereoselektif 1-benzil-3,3-dimetil-5-metilenapirolidina-2,4-dion menggunakan natrium borohidrat dengan logam klorida terpilih]

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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Published in:Malaysian Journal of Analytical Sciences
Main Author: Jumali N.S.; Shaameri Z.; Mohamad H.; Hamzah A.S.
Format: Article
Language:English
Published: Malaysian Society of Analytical Sciences 2017
Online Access:https://www.scopus.com/inward/record.uri?eid=2-s2.0-85031996362&doi=10.17576%2fmjas-2017-2105-22&partnerID=40&md5=fd5bb1310c951daa71c4461055de7cf6
id 2-s2.0-85031996362
spelling 2-s2.0-85031996362
Jumali N.S.; Shaameri Z.; Mohamad H.; Hamzah A.S.
Stereoselective reduction of 1-benzyl-3,3-dimethyl-5-methylenepyrrolidine-2,4-dione using sodium borohydride with selected metal chlorides; [Tindak balas penurunan stereoselektif 1-benzil-3,3-dimetil-5-metilenapirolidina-2,4-dion menggunakan natrium borohidrat dengan logam klorida terpilih]
2017
Malaysian Journal of Analytical Sciences
21
5
10.17576/mjas-2017-2105-22
https://www.scopus.com/inward/record.uri?eid=2-s2.0-85031996362&doi=10.17576%2fmjas-2017-2105-22&partnerID=40&md5=fd5bb1310c951daa71c4461055de7cf6
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,β-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. © 2017, Malaysian Society of Analytical Sciences. All rights reserved.
Malaysian Society of Analytical Sciences
13942506
English
Article
All Open Access; Gold Open Access
author Jumali N.S.; Shaameri Z.; Mohamad H.; Hamzah A.S.
spellingShingle Jumali N.S.; Shaameri Z.; Mohamad H.; Hamzah A.S.
Stereoselective reduction of 1-benzyl-3,3-dimethyl-5-methylenepyrrolidine-2,4-dione using sodium borohydride with selected metal chlorides; [Tindak balas penurunan stereoselektif 1-benzil-3,3-dimetil-5-metilenapirolidina-2,4-dion menggunakan natrium borohidrat dengan logam klorida terpilih]
author_facet Jumali N.S.; Shaameri Z.; Mohamad H.; Hamzah A.S.
author_sort Jumali N.S.; Shaameri Z.; Mohamad H.; Hamzah A.S.
title Stereoselective reduction of 1-benzyl-3,3-dimethyl-5-methylenepyrrolidine-2,4-dione using sodium borohydride with selected metal chlorides; [Tindak balas penurunan stereoselektif 1-benzil-3,3-dimetil-5-metilenapirolidina-2,4-dion menggunakan natrium borohidrat dengan logam klorida terpilih]
title_short Stereoselective reduction of 1-benzyl-3,3-dimethyl-5-methylenepyrrolidine-2,4-dione using sodium borohydride with selected metal chlorides; [Tindak balas penurunan stereoselektif 1-benzil-3,3-dimetil-5-metilenapirolidina-2,4-dion menggunakan natrium borohidrat dengan logam klorida terpilih]
title_full Stereoselective reduction of 1-benzyl-3,3-dimethyl-5-methylenepyrrolidine-2,4-dione using sodium borohydride with selected metal chlorides; [Tindak balas penurunan stereoselektif 1-benzil-3,3-dimetil-5-metilenapirolidina-2,4-dion menggunakan natrium borohidrat dengan logam klorida terpilih]
title_fullStr Stereoselective reduction of 1-benzyl-3,3-dimethyl-5-methylenepyrrolidine-2,4-dione using sodium borohydride with selected metal chlorides; [Tindak balas penurunan stereoselektif 1-benzil-3,3-dimetil-5-metilenapirolidina-2,4-dion menggunakan natrium borohidrat dengan logam klorida terpilih]
title_full_unstemmed Stereoselective reduction of 1-benzyl-3,3-dimethyl-5-methylenepyrrolidine-2,4-dione using sodium borohydride with selected metal chlorides; [Tindak balas penurunan stereoselektif 1-benzil-3,3-dimetil-5-metilenapirolidina-2,4-dion menggunakan natrium borohidrat dengan logam klorida terpilih]
title_sort Stereoselective reduction of 1-benzyl-3,3-dimethyl-5-methylenepyrrolidine-2,4-dione using sodium borohydride with selected metal chlorides; [Tindak balas penurunan stereoselektif 1-benzil-3,3-dimetil-5-metilenapirolidina-2,4-dion menggunakan natrium borohidrat dengan logam klorida terpilih]
publishDate 2017
container_title Malaysian Journal of Analytical Sciences
container_volume 21
container_issue 5
doi_str_mv 10.17576/mjas-2017-2105-22
url https://www.scopus.com/inward/record.uri?eid=2-s2.0-85031996362&doi=10.17576%2fmjas-2017-2105-22&partnerID=40&md5=fd5bb1310c951daa71c4461055de7cf6
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,β-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. © 2017, Malaysian Society of Analytical Sciences. All rights reserved.
publisher Malaysian Society of Analytical Sciences
issn 13942506
language English
format Article
accesstype All Open Access; Gold Open Access
record_format scopus
collection Scopus
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