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Geminal Difunctionalization of Vinylarenes: Concise Synthesis of 1,3-Dioxolan-4-ones

Balaji, Pandur Venkatesan and Chandrasekaran, Srinivasan (2019) Geminal Difunctionalization of Vinylarenes: Concise Synthesis of 1,3-Dioxolan-4-ones. In: SYNLETT, 30 (20). pp. 2263-2267.

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Official URL: http://dx.doi.org/10.1055/s-0039-1690250


We report a straightforward method for the synthesis of five-membered 1,3-dioxolan-4-ones by an unprecedented oxidative alkene geminal difunctionalization strategy using alpha-hydroxy carboxylic acids. Under the geminal oxidative addition conditions, various substituted alpha-hydroxy carboxylic acids and styrenes containing a variety of substituents, including beta-substituted styrenes, were effectively coupled regioselectively (anti-Markovnikov) with an isobutyl-substituted chiral alpha-hydroxy carboxylic acid, providing an annulation with excellent dia--stereoselectivity. An aryl migration in the semipinacol rearrangement leading to geminal oxidative addition of the alpha-hydroxy carboxylic acids was confirmed by deuterium-labelling and control studies.

Item Type: Journal Article
Publication: SYNLETT
Additional Information: Copyright of this article belongs to GEORG THIEME VERLAG KG
Keywords: dioxolanones; geminal difunctionalization; regioselectivity; rearrangement; aryl migration
Department/Centre: Division of Chemical Sciences > Organic Chemistry
Date Deposited: 30 Dec 2019 11:04
Last Modified: 30 Dec 2019 11:04
URI: http://eprints.iisc.ac.in/id/eprint/64244

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