1,3-Dipolar cycloadditions of prop-1-ene-1,3-sultone with nitrile oxides/nitrones

H. Zhang; W. H. Chan; Albert W.M. Lee; W. Y. Wong

doi:10.1016/S0040-4039(02)02502-9

1,3-Dipolar cycloadditions of prop-1-ene-1,3-sultone with nitrile oxides/nitrones

H. Zhang, W. H. Chan^*, Albert W.M. Lee, W. Y. Wong

^*Corresponding author for this work

Department of Chemistry

Research output: Contribution to journal › Journal article › peer-review

28 Citations (Scopus)

Abstract

The scope and limitations of dipolar cycloaddition reactions between nitrile oxides/nitrones and prop-1-ene-1,3-sultone have been investigated. A remarkably high degree of regioselectivity and stereoselectivity was observed. The homochiral sultam 8e was synthesized in a four-step reaction sequence starting from the substituted isoxazoline 4e obtained from the cycloaddition. The absolute stereochemistry of this material was assigned by an X-ray crystallographic investigation of the intermediate 7e.

Original language	English
Pages (from-to)	395-397
Number of pages	3
Journal	Tetrahedron Letters
Volume	44
Issue number	2
DOIs	https://doi.org/10.1016/S0040-4039(02)02502-9
Publication status	Published - 6 Jan 2003

Scopus Subject Areas

Biochemistry
Drug Discovery
Organic Chemistry

Access to Document

10.1016/S0040-4039(02)02502-9

Cite this

@article{2522135c13f34de2b04d430a54660f8d,

title = "1,3-Dipolar cycloadditions of prop-1-ene-1,3-sultone with nitrile oxides/nitrones",

abstract = "The scope and limitations of dipolar cycloaddition reactions between nitrile oxides/nitrones and prop-1-ene-1,3-sultone have been investigated. A remarkably high degree of regioselectivity and stereoselectivity was observed. The homochiral sultam 8e was synthesized in a four-step reaction sequence starting from the substituted isoxazoline 4e obtained from the cycloaddition. The absolute stereochemistry of this material was assigned by an X-ray crystallographic investigation of the intermediate 7e.",

author = "H. Zhang and Chan, {W. H.} and Lee, {Albert W.M.} and Wong, {W. Y.}",

note = "Funding Information: Financial support from the Faculty Research Committee of the Hong Kong Baptist University (FRG/99-00/II-14) and the Research Grant Council of the HKSAR (HKBU 2024/00P) is gratefully acknowledged.",

year = "2003",

month = jan,

day = "6",

doi = "10.1016/S0040-4039(02)02502-9",

language = "English",

volume = "44",

pages = "395--397",

journal = "Tetrahedron Letters",

issn = "0040-4039",

publisher = "Elsevier Ltd.",

number = "2",

}

TY - JOUR

T1 - 1,3-Dipolar cycloadditions of prop-1-ene-1,3-sultone with nitrile oxides/nitrones

AU - Zhang, H.

AU - Chan, W. H.

AU - Lee, Albert W.M.

AU - Wong, W. Y.

N1 - Funding Information: Financial support from the Faculty Research Committee of the Hong Kong Baptist University (FRG/99-00/II-14) and the Research Grant Council of the HKSAR (HKBU 2024/00P) is gratefully acknowledged.

PY - 2003/1/6

Y1 - 2003/1/6

N2 - The scope and limitations of dipolar cycloaddition reactions between nitrile oxides/nitrones and prop-1-ene-1,3-sultone have been investigated. A remarkably high degree of regioselectivity and stereoselectivity was observed. The homochiral sultam 8e was synthesized in a four-step reaction sequence starting from the substituted isoxazoline 4e obtained from the cycloaddition. The absolute stereochemistry of this material was assigned by an X-ray crystallographic investigation of the intermediate 7e.

AB - The scope and limitations of dipolar cycloaddition reactions between nitrile oxides/nitrones and prop-1-ene-1,3-sultone have been investigated. A remarkably high degree of regioselectivity and stereoselectivity was observed. The homochiral sultam 8e was synthesized in a four-step reaction sequence starting from the substituted isoxazoline 4e obtained from the cycloaddition. The absolute stereochemistry of this material was assigned by an X-ray crystallographic investigation of the intermediate 7e.

UR - http://www.scopus.com/inward/record.url?scp=0037420993&partnerID=8YFLogxK

U2 - 10.1016/S0040-4039(02)02502-9

DO - 10.1016/S0040-4039(02)02502-9

M3 - Journal article

AN - SCOPUS:0037420993

SN - 0040-4039

VL - 44

SP - 395

EP - 397

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 2

ER -

1,3-Dipolar cycloadditions of prop-1-ene-1,3-sultone with nitrile oxides/nitrones

Abstract

Scopus Subject Areas

Access to Document

Other files and links

Fingerprint

Cite this