Synthesis of aminoalcohols from substituted alkenes tungstenooxaziridine catalysis

Herein we report the WO 2 Dipic(H 2 O) promoted oxyamination of alkenes using sulfonamides as the quantitative source of N . The reaction works for activated and unactivated alkenes in high yields, diastereoselectivities, and stereospecificity. A catalytic cycle involving the formation of tungstenoo...

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Published in:Organic & biomolecular chemistry 2024-03, Vol.22 (11), p.23-236
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
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Summary:Herein we report the WO 2 Dipic(H 2 O) promoted oxyamination of alkenes using sulfonamides as the quantitative source of N . 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 A as the rate-determining-step has been proposed. Initial kinetic and competition experiments provide evidence for the proposed mechanism. Novel tungstenooxaziridine complex promotes the oxyamination of substituted alkenes with high stereoselectivity and stereospecificity. Mechanistic studies provide evidence for a highly selective syn -difunctionalization pathway.
ISSN:1477-0520
1477-0539
DOI:10.1039/d4ob00022f