Synthesis and Diels-Alder reactions of prop-1-ene-1,3-sultone, and chemical transformations of the Diels-Alder adducts

La Sheng Jiang; Wing Hong CHAN; Albert W M LEE

doi:10.1016/S0040-4020(99)00009-5

Synthesis and Diels-Alder reactions of prop-1-ene-1,3-sultone, and chemical transformations of the Diels-Alder adducts

La Sheng Jiang, Wing Hong CHAN^*, Albert W M LEE

^*Corresponding author for this work

Department of Chemistry

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

25 Citations (Scopus)

Abstract

A reliable and novel synthetic route for the preparation of prop-1-ene- 1,3-sultone (1) has been developed. An overall yield of 34% could be achieved for this five-step synthesis. The Diels-Alder reactions of 1 with a variety of dienes were investigated for the first time and achieved with good chemical yield and excellent endo-selectivity. The subsequent transformations of the Diels-Alder cycloadducts were also explored.

Original language	English
Pages (from-to)	2245-2262
Number of pages	18
Journal	Tetrahedron
Volume	55
Issue number	8
DOIs	https://doi.org/10.1016/S0040-4020(99)00009-5
Publication status	Published - 19 Feb 1999

Scopus Subject Areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/S0040-4020(99)00009-5

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title = "Synthesis and Diels-Alder reactions of prop-1-ene-1,3-sultone, and chemical transformations of the Diels-Alder adducts",

abstract = "A reliable and novel synthetic route for the preparation of prop-1-ene- 1,3-sultone (1) has been developed. An overall yield of 34% could be achieved for this five-step synthesis. The Diels-Alder reactions of 1 with a variety of dienes were investigated for the first time and achieved with good chemical yield and excellent endo-selectivity. The subsequent transformations of the Diels-Alder cycloadducts were also explored.",

author = "Jiang, {La Sheng} and CHAN, {Wing Hong} and LEE, {Albert W M}",

note = "Funding Information: 96/II-75) and the Research Grant Council (HKBU 136/94P) is gratefully acknowledged. Funding Information: Financial support from the Faculty Research Committee of the Hong Kong Baptist University",

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doi = "10.1016/S0040-4020(99)00009-5",

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T1 - Synthesis and Diels-Alder reactions of prop-1-ene-1,3-sultone, and chemical transformations of the Diels-Alder adducts

AU - Jiang, La Sheng

AU - CHAN, Wing Hong

AU - LEE, Albert W M

N1 - Funding Information: 96/II-75) and the Research Grant Council (HKBU 136/94P) is gratefully acknowledged. Funding Information: Financial support from the Faculty Research Committee of the Hong Kong Baptist University

PY - 1999/2/19

Y1 - 1999/2/19

N2 - A reliable and novel synthetic route for the preparation of prop-1-ene- 1,3-sultone (1) has been developed. An overall yield of 34% could be achieved for this five-step synthesis. The Diels-Alder reactions of 1 with a variety of dienes were investigated for the first time and achieved with good chemical yield and excellent endo-selectivity. The subsequent transformations of the Diels-Alder cycloadducts were also explored.

AB - A reliable and novel synthetic route for the preparation of prop-1-ene- 1,3-sultone (1) has been developed. An overall yield of 34% could be achieved for this five-step synthesis. The Diels-Alder reactions of 1 with a variety of dienes were investigated for the first time and achieved with good chemical yield and excellent endo-selectivity. The subsequent transformations of the Diels-Alder cycloadducts were also explored.

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U2 - 10.1016/S0040-4020(99)00009-5

DO - 10.1016/S0040-4020(99)00009-5

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JO - Tetrahedron

JF - Tetrahedron

IS - 8

ER -

Synthesis and Diels-Alder reactions of prop-1-ene-1,3-sultone, and chemical transformations of the Diels-Alder adducts

Abstract

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