An Organocatalytic and Stereoselective Vinylogous Domino Process towards Thiochromans

• Published in: Chemistry : a European journal Vol. 29; no. 42; pp. e202301311 - n/a
• Main Authors: Milbeo, Pierre, Lebrêne, Arthur, Savchuk, Mariia, Vo‐Thanh, Giang, Oudeyer, Sylvain, Beucher, Hélène, Brière, Jean‐François
• Format: Journal Article
• Language: English
• Published: Germany Wiley Subscription Services, Inc 26-07-2023; Wiley-VCH Verlag
• Subjects: Aldehydes; Alkylidene; Catalysis; Chemical Sciences; Chemistry; Cycloaddition; Dienes; Meldrum's acid; Michael addition; Organic chemistry; organocatalysis; Stereoselectivity; sulfur heterocycles; Vinylogy; Michael addition; organocatalysis; Meldrum's acid; Vinylogy; sulfur heterocycles
• ISSN: 0947-6539; 1521-3765
• DOI: 10.1002/chem.202301311

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.
Towards heterocyclic diversity: 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, namely an unprecedented sulfa‐1,6‐conjugate addition and a diastereoselective aldol reaction triggering a formal (4+2) cycloaddition, which opens a new route to bio‐relevant and original tricyclic thiochroman derivatives.