Trisubstituted Highly Activated Benzo[ d]thiazol-2-yl-sulfone-Containing Olefins as Building Blocks in Organic Synthesis

0531602 - ÚEB 2021 RIV US eng J - Journal Article
Kováč, O. - Zálešák, F. - J.-Y. D. Bon, D. - Roiser, L. - Baar, L. V. - Waser, M. - Pospíšil, Jiří
Trisubstituted Highly Activated Benzo[ d]thiazol-2-yl-sulfone-Containing Olefins as Building Blocks in Organic Synthesis.
Journal of Organic Chemistry. Roč. 85, č. 11 (2020), s. 7192-7206. ISSN 0022-3263. E-ISSN 1520-6904
R&D Projects: GA MŠMT(CZ) LO1304; GA MŠMT(CZ) LO1204; GA MŠMT(CZ) EF16_019/0000738
Institutional support: RVO:61389030
Keywords : DIVERSITY-ORIENTED SYNTHESIS * PRACTICAL SYNTHESIS * MICHAEL ACCEPTORS
OECD category: Organic chemistry
Impact factor: 4.354, year: 2020
Method of publishing: Open access
http://doi.org/10.1021/acs.joc.0c00571

In this paper, we report the formation of highly electrophilic 1,1-deactivated olefins, their use as novel synthetic building blocks, and their transformation to structurally diverse molecular scaffolds. Synthesis of 1,1-deactivated olefins substituted with a BT-sulfonyl group and a carbonyl or nitrile, respectively, consists of unusual Ti(OPri)4-mediated Knoevenagel-type condensation and proceed in good to excellent yields. Generated olefins can be further transformed in a highly stereoselective manner and in good yields to various polyfunctionalized heterocycles and acyclic molecular scaffolds. Overall, the obtained structures are accessed in two to four steps starting from the (mostly) commercially available aldehydes. In addition, the presence of the BT-sulfonyl group in prepared structures allows for further chemoselective functionalization/post-synthetic transformations to provide structurally diverse final compounds.
Permanent Link: http://hdl.handle.net/11104/0310234