Issue 18, 2019
From the journal:

Organic Chemistry Frontiers

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

Vojtěch Dočekal, ORCID logo ‡a   Bedřich Formánek, ORCID logo ‡a   Ivana Císařová ORCID logo b  and  Jan Veselý ORCID logo *a  

* Corresponding authors

a Department of Organic Chemistry, Faculty of Science, Charles University, Hlavova 2030/8, 128 43 Prague 2, Czech Republic
E-mail: jan.vesely@natur.cuni.cz
Web: http://orgchem.cz/vesely/

b Department of Inorganic Chemistry, Faculty of Science, Charles University, Hlavova 2030/8, 128 43 Prague 2, Czech Republic

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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Article information

DOI
https://doi.org/10.1039/C9QO00886A
Article type
Research Article
Submitted
12 Jul 2019
Accepted
31 Jul 2019
First published
02 Aug 2019

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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