Indium Mediated Reformatsky-Type Allylation of N-<i>tert</i>-Butanesulfinyl Iminoester with 1,3-Butadiene

This study presents the indium-mediated\nthree-component radical\nReformatsky-type allylation of <i>N</i>-<i>tert</i>-butanesulfinyl iminoester with 1,3-butadiene. This novel approach\noffers a rapid synthesis pathway to valuable homoallylic noncanonical\namino acids, demonstrated with over 30 examples showing nice regio-\nand diastereoselectivity. Mechanism studies revealed that allylindium\ncomplexes served as key intermediates, formed through a single-electron\nreduction of allylic radicals by Indium species.

Publication Details

Journal
Figshare
Published
2024-12-20
DOI
https://doi.org/10.1021/acs.orglett.4c04086.s001
Primary Topic
Radical Photochemical Reactions
Type
article
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article

Indium Mediated Reformatsky-Type Allylation of N-tert-Butanesulfinyl Iminoester with 1,3-Butadiene

Figshare
Radical Photochemical Reactions
article

Indium Mediated Reformatsky-Type Allylation of N-tert-Butanesulfinyl Iminoester with 1,3-Butadiene

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Abstract

This study presents the indium-mediated\nthree-component radical\nReformatsky-type allylation of <i>N</i>-<i>tert</i>-butanesulfinyl iminoester with 1,3-butadiene. This novel approach\noffers a rapid synthesis pathway to valuable homoallylic noncanonical\namino acids, demonstrated with over 30 examples showing nice regio-\nand diastereoselectivity. Mechanism studies revealed that allylindium\ncomplexes served as key intermediates, formed through a single-electron\nreduction of allylic radicals by Indium species.

Figshare
Openalex Percentile: Top 75%
Radical Photochemical Reactions
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Indium Mediated Reformatsky-Type Allylation of N-<i>tert</i>-Butanesulfinyl Iminoester with 1,3-Butadiene · Figshare (2024) | TGRS Research Map | TGRS