Synthesis of Isoxazolidines from Substituted Vinylnitrones and Conjugated Carbonyls via Visible-Light Photocatalysis

Phillip Trieu; William H. Filkin; Ali Pinarci; Elisa M. Tobias; Rufai Madiu; Brandon Dellosso; Justin Roldan; Pulakesh Das; Brooke E. Austin; Gustavo Moura-Letts

doi:10.1002/cptc.202200277

Synthesis of Isoxazolidines from Substituted Vinylnitrones and Conjugated Carbonyls via Visible-Light Photocatalysis

Phillip Trieu
, William H. Filkin
, Ali Pinarci
, Elisa M. Tobias
, Rufai Madiu
, Brandon Dellosso
, Justin Roldan
, Pulakesh Das
, Brooke E. Austin
, Gustavo Moura-Letts

Chemistry

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

3 Scopus citations

Abstract

Herein we report the first redox-neutral visible-light photocatalytic intermolecular dipolar cycloaddition for the diastereoselective synthesis of isoxazolidines. We have found that vinyl nitrones with a diverse substitution pattern undergo visible-light-promoted cycloadditions with conjugated carbonyls in the presence of catalytic amounts of Ru(bpy)₃Cl₂, with the reaction proceeding with high yields and good selectivities. A redox-neutral pathway is proposed as the primary photoredox mechanism for this transformation.

Original language	English (US)
Article number	e202200277
Journal	ChemPhotoChem
Volume	7
Issue number	3
DOIs	https://doi.org/10.1002/cptc.202200277
State	Published - Mar 2023

All Science Journal Classification (ASJC) codes

Analytical Chemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1002/cptc.202200277

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title = "Synthesis of Isoxazolidines from Substituted Vinylnitrones and Conjugated Carbonyls via Visible-Light Photocatalysis",

abstract = "Herein we report the first redox-neutral visible-light photocatalytic intermolecular dipolar cycloaddition for the diastereoselective synthesis of isoxazolidines. We have found that vinyl nitrones with a diverse substitution pattern undergo visible-light-promoted cycloadditions with conjugated carbonyls in the presence of catalytic amounts of Ru(bpy)3Cl2, with the reaction proceeding with high yields and good selectivities. A redox-neutral pathway is proposed as the primary photoredox mechanism for this transformation.",

author = "Phillip Trieu and Filkin, \{William H.\} and Ali Pinarci and Tobias, \{Elisa M.\} and Rufai Madiu and Brandon Dellosso and Justin Roldan and Pulakesh Das and Austin, \{Brooke E.\} and Gustavo Moura-Letts",

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year = "2023",

month = mar,

doi = "10.1002/cptc.202200277",

language = "English (US)",

volume = "7",

journal = "ChemPhotoChem",

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T1 - Synthesis of Isoxazolidines from Substituted Vinylnitrones and Conjugated Carbonyls via Visible-Light Photocatalysis

AU - Trieu, Phillip

AU - Filkin, William H.

AU - Pinarci, Ali

AU - Tobias, Elisa M.

AU - Madiu, Rufai

AU - Dellosso, Brandon

AU - Roldan, Justin

AU - Das, Pulakesh

AU - Austin, Brooke E.

AU - Moura-Letts, Gustavo

PY - 2023/3

Y1 - 2023/3

N2 - Herein we report the first redox-neutral visible-light photocatalytic intermolecular dipolar cycloaddition for the diastereoselective synthesis of isoxazolidines. We have found that vinyl nitrones with a diverse substitution pattern undergo visible-light-promoted cycloadditions with conjugated carbonyls in the presence of catalytic amounts of Ru(bpy)3Cl2, with the reaction proceeding with high yields and good selectivities. A redox-neutral pathway is proposed as the primary photoredox mechanism for this transformation.

AB - Herein we report the first redox-neutral visible-light photocatalytic intermolecular dipolar cycloaddition for the diastereoselective synthesis of isoxazolidines. We have found that vinyl nitrones with a diverse substitution pattern undergo visible-light-promoted cycloadditions with conjugated carbonyls in the presence of catalytic amounts of Ru(bpy)3Cl2, with the reaction proceeding with high yields and good selectivities. A redox-neutral pathway is proposed as the primary photoredox mechanism for this transformation.

UR - https://www.scopus.com/pages/publications/85143291054

UR - https://www.scopus.com/pages/publications/85143291054#tab=citedBy

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DO - 10.1002/cptc.202200277

M3 - Article

AN - SCOPUS:85143291054

SN - 2367-0932

VL - 7

JO - ChemPhotoChem

JF - ChemPhotoChem

IS - 3

M1 - e202200277

ER -

Synthesis of Isoxazolidines from Substituted Vinylnitrones and Conjugated Carbonyls via Visible-Light Photocatalysis

Abstract

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