Synthesis of aminoalcohols from substituted alkenes via tungstenooxaziridine catalysis

Rufai Madiu; Brandon Dellosso; Erin L. Doran; Jenna M. Doran; Ali A. Pinarci; Tyler M. TenHoeve; Amari M. Howard; James L. Stroud; Dominic A. Rivera; Dylan A. Moskovitz; Steven J. Finneran; Alyssa N. Singer; Morgan E. Rossi; Gustavo Moura-Letts

doi:10.1039/d4ob00022f

Synthesis of aminoalcohols from substituted alkenes via tungstenooxaziridine catalysis

Rufai Madiu, Brandon Dellosso, Erin L. Doran, Jenna M. Doran, Ali A. Pinarci, Tyler M. TenHoeve, Amari M. Howard, James L. Stroud, Dominic A. Rivera, Dylan A. Moskovitz, Steven J. Finneran, Alyssa N. Singer, Morgan E. Rossi, Gustavo Moura-Letts

Chemistry

Research output: Contribution to journal › Article › peer-review

5 Scopus citations

Abstract

Herein we report the WO₂Dipic(H₂O) 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.

Original language	English (US)
Pages (from-to)	2300-2306
Number of pages	7
Journal	Organic and Biomolecular Chemistry
Volume	22
Issue number	11
DOIs	https://doi.org/10.1039/d4ob00022f
State	Published - Feb 21 2024

All Science Journal Classification (ASJC) codes

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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Madiu, R., Dellosso, B., Doran, E. L., Doran, J. M., Pinarci, A. A., TenHoeve, T. M., Howard, A. M., Stroud, J. L., Rivera, D. A., Moskovitz, D. A., Finneran, S. J., Singer, A. N., Rossi, M. E., & Moura-Letts, G. (2024). Synthesis of aminoalcohols from substituted alkenes via tungstenooxaziridine catalysis. Organic and Biomolecular Chemistry, 22(11), 2300-2306. https://doi.org/10.1039/d4ob00022f

@article{7e3751c6fe4d489eb6e5e0ebef2c08bb,

title = "Synthesis of aminoalcohols from substituted alkenes via tungstenooxaziridine catalysis",

abstract = "Herein we report the WO2Dipic(H2O) 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.",

author = "Rufai Madiu and Brandon Dellosso and Doran, \{Erin L.\} and Doran, \{Jenna M.\} and Pinarci, \{Ali A.\} and TenHoeve, \{Tyler M.\} and Howard, \{Amari M.\} and Stroud, \{James L.\} and Rivera, \{Dominic A.\} and Moskovitz, \{Dylan A.\} and Finneran, \{Steven J.\} and Singer, \{Alyssa N.\} and Rossi, \{Morgan E.\} and Gustavo Moura-Letts",

note = "Publisher Copyright: {\textcopyright} 2024 The Royal Society of Chemistry.",

year = "2024",

month = feb,

day = "21",

doi = "10.1039/d4ob00022f",

language = "English (US)",

volume = "22",

pages = "2300--2306",

journal = "Organic and Biomolecular Chemistry",

issn = "1477-0520",

publisher = "Royal Society of Chemistry",

number = "11",

}

Madiu, R, Dellosso, B, Doran, EL, Doran, JM, Pinarci, AA, TenHoeve, TM, Howard, AM, Stroud, JL, Rivera, DA, Moskovitz, DA, Finneran, SJ, Singer, AN, Rossi, ME & Moura-Letts, G 2024, 'Synthesis of aminoalcohols from substituted alkenes via tungstenooxaziridine catalysis', Organic and Biomolecular Chemistry, vol. 22, no. 11, pp. 2300-2306. https://doi.org/10.1039/d4ob00022f

TY - JOUR

T1 - Synthesis of aminoalcohols from substituted alkenes via tungstenooxaziridine catalysis

AU - Madiu, Rufai

AU - Dellosso, Brandon

AU - Doran, Erin L.

AU - Doran, Jenna M.

AU - Pinarci, Ali A.

AU - TenHoeve, Tyler M.

AU - Howard, Amari M.

AU - Stroud, James L.

AU - Rivera, Dominic A.

AU - Moskovitz, Dylan A.

AU - Finneran, Steven J.

AU - Singer, Alyssa N.

AU - Rossi, Morgan E.

AU - Moura-Letts, Gustavo

PY - 2024/2/21

Y1 - 2024/2/21

N2 - Herein we report the WO2Dipic(H2O) 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.

AB - Herein we report the WO2Dipic(H2O) 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.

UR - https://www.scopus.com/pages/publications/85187626358

UR - https://www.scopus.com/inward/citedby.url?scp=85187626358&partnerID=8YFLogxK

U2 - 10.1039/d4ob00022f

DO - 10.1039/d4ob00022f

M3 - Article

C2 - 38410027

AN - SCOPUS:85187626358

SN - 1477-0520

VL - 22

SP - 2300

EP - 2306

JO - Organic and Biomolecular Chemistry

JF - Organic and Biomolecular Chemistry

IS - 11

ER -

Synthesis of aminoalcohols from substituted alkenes via tungstenooxaziridine catalysis

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