Publication details
Stereoselective michael addition of benzo[b]thiophene-1,1-dioxide derivatives
| Authors | |
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| Year of publication | 2025 |
| Type | Appeared in Conference without Proceedings |
| MU Faculty or unit | |
| Citation | |
| Description | Michael addition is a key carbon–carbon bond-forming reaction between nucleophiles and electron-deficient alkenes. This reaction is highly attractive for stereoselective organocatalysis due to the diverse range of possible nucleophilic and electrophilic partners. Moreover, it enables the synthesis of highly complex molecules in a single step. Benzo[b]thiophene-1,1-dioxide and its derivatives represent a novel class of powerful Michael acceptors. Its structural motif is found in numerous biologically and pharmaceutically active compounds. Additionally, incorporating electron-withdrawing groups into the structure could enhance its reactivity further. Phenols were found to be the most suitable nucleophilic partners in reactions with benzo[b]thiophene-1,1-dioxide derivatives. Benzo[b]thiophene-1,1-dioxide substrates were modified and screened to identify the most suitable electrophilic structures. Among the tested compounds, the 2-trifluoromethyl acetyl derivative of benzo[b]thiophene-1,1-dioxide displayed the highest reactivity and stereoselectivity. In the next phase, selected chiral bifunctional organocatalysts were examined for their ability to catalyze the stereoselective Michael addition. The resulting products were analyzed using chiral HPLC and NMR techniques to determine enantiomeric ratios (er), diastereomeric ratios (d.r.), and conversion rates. Preliminary experiments yielded Michael adducts with excellent yields and good diastereoselectivity (d.r. up to 86:14), although moderate enantioselectivity was observed (e.r. up to 67:33). While there is enough room for further improvements, these results highlight the synthetic capability of the benzo[b]thiophene-1,1-dioxide scaffold as an appealing electrophilic partner. |
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