Setembro 2013 vol. 1 num. 1 - Brazilian Meeting on Organic Synthesis 2011

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An efficient preparation of α-diketones.

Machado, Shirley Muniz ; Sousa, Fabiana Garcia de ; Silva, Gil Valdo José da ;

Abstract:

Cyclic α,β-epoxy ketones are valuable synthetic intermediates due to their high reactivity. Various products resulting from rearrangements of cyclic 2,3- epoxy ketones are important starting materials for the synthesis of perfumes, synthetic food flavorings, and pharmaceuticals. Lewis acid catalyzed ring opening of these epoxides usually follow some well defined paths: the intermediate carbocation is always formed in the carbon atom farther from the carbonyl group (III) (Scheme 1), because this group destabilizes positive charges in -position. The carbocation can either undergo acyl migration or H+ elimination (or hydrogen migration) to form a ring-contracted aldehyde (A) or an - diketone (B) (Scheme 1). Scheme 1: Lewis acid catalyzed rearrangement of cyclic 2,3-epoxy ketones.

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Palavras-chave: Lewis acid, 1, 3-diketone and 1, 2-diketone,

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DOI: 10.5151/chempro-14bmos-R0099-1

Referências bibliográficas
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Como citar:

Machado, Shirley Muniz; Sousa, Fabiana Garcia de; Silva, Gil Valdo José da; "An efficient preparation of α-diketones.", p. 99 . In: In Blucher Chemistry Proceedings, São Paulo, v. 1, n. 1, Setembro.2013. São Paulo: Blucher, 2013.
ISSN 2318-4043, DOI 10.5151/chempro-14bmos-R0099-1

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