Geminal Difunctionalization of Vinylarenes: Concise Synthesis of 1,3-Dioxolan-4-ones
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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 α-hydroxy carboxylic acids. Under the geminal oxidative addition conditions, various substituted α-hydroxy carboxylic acids and styrenes containing a variety of substituents, including β-substituted styrenes, were effectively coupled regioselectively (anti-Markovnikov) with an isobutyl-substituted chiral α-hydroxy carboxylic acid, providing an annulation with excellent diastereoselectivity. An aryl migration in the semipinacol rearrangement leading to geminal oxidative addition of the α-hydroxy carboxylic acids was confirmed by deuterium-labelling and control studies.
2018 ◽
Vol 21
(4)
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pp. 298-301
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2007 ◽
Vol 51
(2)
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pp. 225-233
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2016 ◽
Vol 2016
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pp. 1-8
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