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Issue 18, 2019
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A formal [4 + 2] cycloaddition of sulfur-containing alkylidene heterocycles with allenic compounds

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Abstract

In this study, we report an enantioselective synthesis of sulfur heterocycles containing the dihydro-2H-pyran moiety. The synthesis strategy is based on quinidine catalyzed formal [4 + 2] cycloaddition between 3-alkylidene benzo[b]thiophenes and allenoates, affording the corresponding cycloadducts in high yields (up to 95%) with high enantioselectivities (up to 99% ee). Moreover, cycloadducts can be isolated by simple filtration from the reaction media.

Graphical abstract: A formal [4 + 2] cycloaddition of sulfur-containing alkylidene heterocycles with allenic compounds

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Publication details

The article was received on 12 Jul 2019, accepted on 31 Jul 2019 and first published on 02 Aug 2019


Article type: Research Article
DOI: 10.1039/C9QO00886A
Org. Chem. Front., 2019,6, 3259-3263

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    A formal [4 + 2] cycloaddition of sulfur-containing alkylidene heterocycles with allenic compounds

    V. Dočekal, B. Formánek, I. Císařová and J. Veselý, Org. Chem. Front., 2019, 6, 3259
    DOI: 10.1039/C9QO00886A

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