Organocatalytic stereoselective construction of polycyclic benzo[]thiophenes from 2-aminobenzo[]thiophenes and alkynyl-substituted enones
A highly efficient protocol for stereoselective synthesis of novel polycyclic benzo[ b ]thiophene derivatives was developed. Using quinine-derived bifunctional thiourea (5 mol%) as a catalyst, asymmetric [3+3] annulation of N -(benzo[ b ]thiophen-2-yl)-sulfonamide with 2-alkynyl cycloenone could pro...
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Veröffentlicht in: | New journal of chemistry 2023-07, Vol.47 (3), p.14515-14519 |
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Hauptverfasser: | , , |
Format: | Artikel |
Sprache: | eng |
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Zusammenfassung: | A highly efficient protocol for stereoselective synthesis of novel polycyclic benzo[
b
]thiophene derivatives was developed. Using quinine-derived bifunctional thiourea (5 mol%) as a catalyst, asymmetric [3+3] annulation of
N
-(benzo[
b
]thiophen-2-yl)-sulfonamide with 2-alkynyl cycloenone could provide dihydrobenzo[4,5]thieno[2,3-
b
]pyridine derivatives in moderate to good yields (up to 93%) with mostly excellent enantioselectivities (up to 97% ee) under mild conditions. In addition, large-scale experiments and derivatizations were explored. In particular, the target product in large-scale experiments could be easily purified by filtration and the filtrated product showed >99% ee.
Bifunctional thiourea-catalyzed asymmetric [3+3] annulation of 2-aminobenzothiophenes with alkynyl-substituted enones for enantioselective synthesis of polycyclic benzothiophenes with high stereoselectivities was developed. |
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ISSN: | 1144-0546 1369-9261 |
DOI: | 10.1039/d3nj02798h |