Synthesis of 4-Isoxazolines through Gold(I)-Catalyzed Cyclization of Propargylic N-Hydroxylamines

B. Chandrasekhar; Sewon Ahn; Jae Sang Ryu

doi:10.1021/acs.joc.6b01499

Synthesis of 4-Isoxazolines through Gold(I)-Catalyzed Cyclization of Propargylic N-Hydroxylamines

B. Chandrasekhar, Sewon Ahn, Jae Sang Ryu

Department of Pharmaceutical Sciences

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

25 Scopus citations

Abstract

New catalytic methods for the synthesis of 4-isoxazolines have been developed via catalytic intramolecular cyclizations of propargylic N-hydroxylamines. The reactions proceed rapidly in less than 1 h at room temperature in the presence of 5 mol % (PPh₃)AuCl/5 mol % AgOTf or 5 mol % (PPh₃)AuNTf₂. This process features an efficient route to 4-isoxazolines with high yields, short reaction times, and mild reaction conditions.

Original language	English
Pages (from-to)	6740-6749
Number of pages	10
Journal	Journal of Organic Chemistry
Volume	81
Issue number	15
DOIs	https://doi.org/10.1021/acs.joc.6b01499
State	Published - 5 Aug 2016

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© 2016 American Chemical Society.

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title = "Synthesis of 4-Isoxazolines through Gold(I)-Catalyzed Cyclization of Propargylic N-Hydroxylamines",

abstract = "New catalytic methods for the synthesis of 4-isoxazolines have been developed via catalytic intramolecular cyclizations of propargylic N-hydroxylamines. The reactions proceed rapidly in less than 1 h at room temperature in the presence of 5 mol \% (PPh3)AuCl/5 mol \% AgOTf or 5 mol \% (PPh3)AuNTf2. This process features an efficient route to 4-isoxazolines with high yields, short reaction times, and mild reaction conditions.",

author = "B. Chandrasekhar and Sewon Ahn and Ryu, \{Jae Sang\}",

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doi = "10.1021/acs.joc.6b01499",

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T1 - Synthesis of 4-Isoxazolines through Gold(I)-Catalyzed Cyclization of Propargylic N-Hydroxylamines

AU - Chandrasekhar, B.

AU - Ahn, Sewon

AU - Ryu, Jae Sang

PY - 2016/8/5

Y1 - 2016/8/5

N2 - New catalytic methods for the synthesis of 4-isoxazolines have been developed via catalytic intramolecular cyclizations of propargylic N-hydroxylamines. The reactions proceed rapidly in less than 1 h at room temperature in the presence of 5 mol % (PPh3)AuCl/5 mol % AgOTf or 5 mol % (PPh3)AuNTf2. This process features an efficient route to 4-isoxazolines with high yields, short reaction times, and mild reaction conditions.

AB - New catalytic methods for the synthesis of 4-isoxazolines have been developed via catalytic intramolecular cyclizations of propargylic N-hydroxylamines. The reactions proceed rapidly in less than 1 h at room temperature in the presence of 5 mol % (PPh3)AuCl/5 mol % AgOTf or 5 mol % (PPh3)AuNTf2. This process features an efficient route to 4-isoxazolines with high yields, short reaction times, and mild reaction conditions.

UR - https://www.scopus.com/pages/publications/84981240524

U2 - 10.1021/acs.joc.6b01499

DO - 10.1021/acs.joc.6b01499

M3 - Article

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SN - 0022-3263

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SP - 6740

EP - 6749

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

IS - 15

ER -

Synthesis of 4-Isoxazolines through Gold(I)-Catalyzed Cyclization of Propargylic N-Hydroxylamines

Abstract

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