Synthesis of 2,3-dihydroisoxazoles from propargylic N-hydroxylamines via Zn(II)-catalyzed ring-closure reaction

Patrick Aschwanden; Doug E. Frantz; Erick M. Carreira

doi:10.1021/ol006095r

Synthesis of 2,3-dihydroisoxazoles from propargylic N-hydroxylamines via Zn(II)-catalyzed ring-closure reaction

Patrick Aschwanden
, Doug E. Frantz
, Erick M. Carreira

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

112 Scopus citations

Abstract

(equation presented) A novel cyclization reaction of propargylic N-hydroxylamines to 2,3,5-trisubstituted 2,3-dihydroisoxazoles in the presence of catalytic amounts (10 mol %) of ZnI₂ and DMAP is reported. The methodology provides a mild new approach to this useful class of substituted heterocycles that complements extant methods. The unique reactivity of the propargylic N-hydroxylamine substrates in the presence of Zn(II) and DMAP may have additional applications in other, related alkyne cyclization reactions.

Original language	English
Pages (from-to)	2331-2333
Number of pages	3
Journal	Organic Letters
Volume	2
Issue number	15
DOIs	https://doi.org/10.1021/ol006095r
State	Published - Jul 27 2000

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title = "Synthesis of 2,3-dihydroisoxazoles from propargylic N-hydroxylamines via Zn(II)-catalyzed ring-closure reaction",

abstract = "(equation presented) A novel cyclization reaction of propargylic N-hydroxylamines to 2,3,5-trisubstituted 2,3-dihydroisoxazoles in the presence of catalytic amounts (10 mol \%) of ZnI2 and DMAP is reported. The methodology provides a mild new approach to this useful class of substituted heterocycles that complements extant methods. The unique reactivity of the propargylic N-hydroxylamine substrates in the presence of Zn(II) and DMAP may have additional applications in other, related alkyne cyclization reactions.",

author = "Patrick Aschwanden and Frantz, \{Doug E.\} and Carreira, \{Erick M.\}",

year = "2000",

month = jul,

day = "27",

doi = "10.1021/ol006095r",

language = "English",

volume = "2",

pages = "2331--2333",

journal = "Organic Letters",

issn = "1523-7060",

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T1 - Synthesis of 2,3-dihydroisoxazoles from propargylic N-hydroxylamines via Zn(II)-catalyzed ring-closure reaction

AU - Aschwanden, Patrick

AU - Frantz, Doug E.

AU - Carreira, Erick M.

PY - 2000/7/27

Y1 - 2000/7/27

N2 - (equation presented) A novel cyclization reaction of propargylic N-hydroxylamines to 2,3,5-trisubstituted 2,3-dihydroisoxazoles in the presence of catalytic amounts (10 mol %) of ZnI2 and DMAP is reported. The methodology provides a mild new approach to this useful class of substituted heterocycles that complements extant methods. The unique reactivity of the propargylic N-hydroxylamine substrates in the presence of Zn(II) and DMAP may have additional applications in other, related alkyne cyclization reactions.

AB - (equation presented) A novel cyclization reaction of propargylic N-hydroxylamines to 2,3,5-trisubstituted 2,3-dihydroisoxazoles in the presence of catalytic amounts (10 mol %) of ZnI2 and DMAP is reported. The methodology provides a mild new approach to this useful class of substituted heterocycles that complements extant methods. The unique reactivity of the propargylic N-hydroxylamine substrates in the presence of Zn(II) and DMAP may have additional applications in other, related alkyne cyclization reactions.

UR - https://www.scopus.com/pages/publications/0000521341

U2 - 10.1021/ol006095r

DO - 10.1021/ol006095r

M3 - Article

AN - SCOPUS:0000521341

SN - 1523-7060

VL - 2

SP - 2331

EP - 2333

JO - Organic Letters

JF - Organic Letters

IS - 15

ER -

Synthesis of 2,3-dihydroisoxazoles from propargylic N-hydroxylamines via Zn(II)-catalyzed ring-closure reaction

Abstract

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