An Organocatalytic and Stereoselective Vinylogous Domino Process towards Thiochromans

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.

Automated summary

A highly diastereoselective organocatalyzed domino vinylogous sulfa-Michael-aldol-cyclocondensation (VMAC) reaction has been developed using alkylidene Meldrum's acid as dienes, showcasing an unprecedented sulfa-1,6-conjugate addition and a diastereoselective aldol reaction leading to a formal (4+2) cycloaddition. This research provides a new approach to synthesize bio-relevant and original tricyclic thiochroman derivatives.