An Organocatalytic and Stereoselective Vinylogous Domino Process towards Thiochromans

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

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.