Jamal Hassan

Work

Subjects:

Chemistry

Research Keywords:

The research that I did during my PhD led to the discovery and publication of a novel method for the preparation of α-formyl ketones, by reacting α-substituted ketones with chloroiminium salts derived from the reaction of N,N-dimethylformamide with oxalyl chloride (or phosphorus oxychloride). The reaction proceeds via the formation of a chloroiminium salt which, when hydrolyzed during work up with aqueous base, gives α-formyl ketones in reasonable to good yields. The beauty of the transformation is its simplicity, and the relatively cheap and readily available reagents that it uses. My research interest is the extension of this methodology to the synthesis of chiral chloroiminium salts for use in asymmetric synthesis. Initial experiments that I conducted previously, showed that the chiral chloroiminium salt derived from the reaction of L-proline with oxalyl chloride, reacts with α-substituted ketones asymmetrically, with attack occurring preferentially at one face of the chloroiminium ion intermediate. Subsequent work up with aqueous base affords a non-racemic mixture of the two enantiomers of the α-formyl ketone product. That the product mixture is non-racemic was demonstrated by reductive amination of a crude mixture of the two enantiomers, to form a pair of diastereomeric aminoketones, whose relative amounts were determined by proton NMR spectroscopic analysis of the crude mixture; diastereomeric ratios of up to 4:1 were observed. I would like to pursue this line of inquiry further, and synthesize, and characterize, more chiral formamides with a view to developing them as viable tools in the asymmetric synthesis of other substrates, in addition to α-substituted ketones.

Collaboration interests:

I am interested in collaborating with other researchers in the area of asymmetric synthesis.

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