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Content archived on 2024-04-15

STUDY OF THE ENANTIOSELECTIVE SUBSTRATE RECOGNITION BY CHIRAL ORGANOCOPPER REAGENTS. STRUCTURAL FEATURES OF REACTING SPECIES AND APPLICATIONS IN ASYMMETRIC SYNTHESES

Objective


Organocopper reagents are of importance in organic synthesis because of their versatile reactivity pattern including cross coupling and 1,4-conjugate addition as well as SN2 and SN2' displacement reactions. Their use has made available an overwhelming number of new, and often very short, synthetic pathways to valuable molecules like prostanoids, pheromones, antitumour compounds and fragrance compounds.

As many of these target molecules are chiral, a direct need for control of the absolute configuration in their synthesis emerged for environmental and biological reasons. It is this aspect that has been addressed in the present work.

Novel types of ortho-functionalised arylcopper compounds were synthesised and structurally characterised. A new chiral arenethiolatecopper(I) compound was synthesised, which appeared to be a promising catalyst (9 mole %) for the enantioselective 1,4-addition of methylmagnesium halide to benzylideneacetone. Unprecedented selective exchange reactions between organolithium, organocopper and organomagnesium reagents and arenethiolatecopper(I) compounds have been established and structurally characterised.

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WISE & MUNRO LEARNING RESEARCH
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