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

Pharmaceutical Sciences

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

18 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

Bibliographical note

Funding Information:
This research was supported by the Basic Science Research Program through the National Research Foundation of Korea (NRF) funded by the Ministry of Science, ICT and future Planning (NRF-2015R1A2A2A01004511 and NRF- 2014R1A2A1A11050112).

Publisher Copyright:
© 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}",

note = "Funding Information: This research was supported by the Basic Science Research Program through the National Research Foundation of Korea (NRF) funded by the Ministry of Science, ICT and future Planning (NRF-2015R1A2A2A01004511 and NRF- 2014R1A2A1A11050112). Publisher Copyright: {\textcopyright} 2016 American Chemical Society.",

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AU - Ahn, Sewon

AU - Ryu, Jae Sang

N1 - Funding Information: This research was supported by the Basic Science Research Program through the National Research Foundation of Korea (NRF) funded by the Ministry of Science, ICT and future Planning (NRF-2015R1A2A2A01004511 and NRF- 2014R1A2A1A11050112). Publisher Copyright: © 2016 American Chemical Society.

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.

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

Abstract

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