Stereoselective reduction of 1-benzyl-3,3-dimethyl-5-methylenepyrrolidine-2,4-dione using sodium borohydride with selected metal chlorides

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

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Abstract

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

Item Type:	Article (Journal)
Additional Information:	7370/60337
Uncontrolled Keywords:	Exo-alkene, Metal borohydride, Reduction, Stereoselective
Subjects:	Q Science > QD Chemistry
Kulliyyahs/Centres/Divisions/Institutes (Can select more than one option. Press CONTROL button):	Kulliyyah of Science > Department of Chemistry
Depositing User:	Asst. Prof. Dr Nor Saliyana Jumali
Date Deposited:	26 Dec 2017 11:06
Last Modified:	26 Dec 2017 11:08
URI:	http://irep.iium.edu.my/id/eprint/60337

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