Regioselective, Lewis Acid-Catalyzed Ring-Openings of 2,3-Aziridyl Alcohols with Azoles

The Journal of Organic Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: April 25, 2025

Methods for regioselective ring-opening reactions of N-sulfonyl-protected aziridyl alcohols with azole nucleophiles have been developed. Several classes azoles, including indazole, substituted pyrazole, benzotriazole, and tetrazole, employed as reaction partners, giving rise to C3-selective opening >3:1 N-selectivity. BF3•OEt2 is the optimal catalyst most substrate combinations, although examples where diphenylborinic acid (Ph2BOH) provides higher yields, or proceed efficiently without a catalyst, are also described. Computational modeling BF3•OEt2-catalyzed consistent observed regiochemical outcome. The calculated transition state appears be stabilized by an unconventional OH···FB hydrogen-bonding interaction.

Language: Английский

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Nickel-Catalyzed Cross-Coupling of Aziridines with Thioesters toward Atom-Economic Synthesis of β-Sulfanyl Amides

Organic Letters, Journal Year: 2024, Volume and Issue: 26(40), P. 8457 - 8462

Published: Sept. 27, 2024

Thioesters have been recognized as a class of powerful bifunctional reagents, namely, great donors acyl and sulfide moieties. However, such application in value-added synthesis is still very limited to date. Herein, nickel-catalyzed cross-coupling reaction system aziridines with thioesters was developed under redox-neutral mild conditions. This catalytic method provides an atom-economic route for the diverse β-sulfanyl amide derivatives wide substrate scope (43 examples), good functional group tolerance, regioselectivity.

Language: Английский

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Regioselective Ring Opening of Aziridines by Oximes via C–C Bond Cleavage: Access to a Library of Oxime-Ethers

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: unknown

Published: Dec. 6, 2024

A series of sulfonamido-substituted oxime-ethers have been synthesized by the reaction donor-acceptor aziridines with aldo- and keto-oximes through C-C bond cleavage. Nucleophilic attack an oxime hydroxyl group on

Language: Английский

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H3PO3 promoted reactions of thioamides with 2-substituted benzyl alcohols

Organic & Biomolecular Chemistry, Journal Year: 2024, Volume and Issue: unknown

Published: Dec. 16, 2024

In this study, we have investigated the reactivity of thioamides with alcohols by utilizing H

Language: Английский

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