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. 2023 Jul 26;29(42):e202301311.
doi: 10.1002/chem.202301311. Epub 2023 Jun 19.

An Organocatalytic and Stereoselective Vinylogous Domino Process towards Thiochromans

Pierre Milbeo  1 , Arthur Lebrêne  1 , Mariia Savchuk  1 , Giang Vo-Thanh  2 , Sylvain Oudeyer  1 , Hélène Beucher  1 , Jean-François Brière  1
Affiliations

An Organocatalytic and Stereoselective Vinylogous Domino Process towards Thiochromans

Pierre Milbeo et al. Chemistry. .

Abstract

A highly diastereoselective organocatalyzed domino vinylogous sulfa-Michael-aldol-cyclocondensation (VMAC) reaction has been developed using alkylidene Meldrum's acid as dienes highlighting two vinylogous steps, an unprecedented sulfa-1,6-conjugate addition and a diastereoselective aldol reaction triggering a formal (4+2) cycloaddition. This work opens a new route towards bio-relevant and original tricyclic thiochroman derivatives.

Keywords: Meldrum's acid; Michael addition; Vinylogy; organocatalysis; sulfur heterocycles.

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