Catalyst-Controlled\n[3 + 2] Annulation of Allenes\nwith <i>N</i>‑Monosubstituted Hydroxylamines for\nRegioselective Synthesis of Two Types of Isomeric Isoxazolidines

Catalyst-controlled regioselective [3 + 2] cascade annulation\nof\nallenes with <i>N</i>-monosubstituted hydroxylamines for\nprecise construction of two types of isoxazolidine regiomers has been\ndeveloped. The Ce(OTf)<sub>3</sub> and MgCl<sub>2</sub> can guide\nthe nitrogen and oxygen atoms of <i>N</i>-hydroxyarylamides\nto both ends of the consecutive double bond of allenes, respectively,\nto afford two kinds of isomeric products. Notably and remarkably,\nthe consecutive double bond of allenes served as a C3 synthon.

Publication Details

Journal
Figshare
Published
2024-08-20
DOI
https://doi.org/10.1021/acs.orglett.4c02721.s001
Primary Topic
Catalytic C–H Functionalization Methods
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article
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article

Catalyst-Controlled\n[3 + 2] Annulation of Allenes\nwith N‑Monosubstituted Hydroxylamines for\nRegioselective Synthesis of Two Types of Isomeric Isoxazolidines

Figshare
Catalytic C–H Functionalization Methods
article

Catalyst-Controlled\n[3 + 2] Annulation of Allenes\nwith N‑Monosubstituted Hydroxylamines for\nRegioselective Synthesis of Two Types of Isomeric Isoxazolidines

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Abstract

Catalyst-controlled regioselective [3 + 2] cascade annulation\nof\nallenes with <i>N</i>-monosubstituted hydroxylamines for\nprecise construction of two types of isoxazolidine regiomers has been\ndeveloped. The Ce(OTf)<sub>3</sub> and MgCl<sub>2</sub> can guide\nthe nitrogen and oxygen atoms of <i>N</i>-hydroxyarylamides\nto both ends of the consecutive double bond of allenes, respectively,\nto afford two kinds of isomeric products. Notably and remarkably,\nthe consecutive double bond of allenes served as a C3 synthon.

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Catalytic C–H Functionalization Methods
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Catalyst-Controlled\n[3 + 2] Annulation of Allenes\nwith <i>N</i>‑Monosubstituted Hydroxylamines for\nRegioselective Synthesis of Two Types of Isomeric Isoxazolidines · Figshare (2024) | TGRS Research Map | TGRS