Synthesis of aminoalcohols from substituted alkenes via tungstenooxaziridine catalysis

Herein we report the WO Dipic(H O) promoted oxyamination of alkenes using sulfonamides as the quantitative source of . The reaction works for activated and unactivated alkenes in high yields, diastereoselectivities, and stereospecificity. A catalytic cycle involving the formation of tungstenooxaziri...

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Bibliographic Details
Published in:Organic & biomolecular chemistry 2024-03, Vol.22 (11), p.2300-2306
Main Authors: Madiu, Rufai, Dellosso, Brandon, Doran, Erin L, Doran, Jenna M, Pinarci, Ali A, TenHoeve, Tyler M, Howard, Amari M, Stroud, James L, Rivera, Dominic A, Moskovitz, Dylan A, Finneran, Steven J, Singer, Alyssa N, Rossi, Morgan E, Moura-Letts, Gustavo
Format: Article
Language:English
Subjects:
Alkenes
Catalysis
Catalysts
Stereospecificity
Sulfonamides
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Summary:Herein we report the WO Dipic(H O) promoted oxyamination of alkenes using sulfonamides as the quantitative source of . The reaction works for activated and unactivated alkenes in high yields, diastereoselectivities, and stereospecificity. A catalytic cycle involving the formation of tungstenooxaziridine complex 1 as the active catalyst and hydrolysis of tungstenooxazolidine intermediate as the rate-determining-step has been proposed. Initial kinetic and competition experiments provide evidence for the proposed mechanism.
ISSN:1477-0520
1477-0539
DOI:10.1039/d4ob00022f