Synthesis of chiral sultams and their application as chiral auxiliaries in an asymmetric Diels-Alder reaction

Hong Kui Zhang; Wing Hong Chan; Albert W. M. Lee; Wai Yeung Wong; Ping Fang Xia

doi:10.1016/j.tetasy.2004.12.026

Synthesis of chiral sultams and their application as chiral auxiliaries in an asymmetric Diels-Alder reaction

Hong Kui Zhang, Wing Hong Chan^*, Albert W. M. Lee, Wai Yeung Wong, Ping Fang Xia

^*Corresponding author for this work

Department of Chemistry

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

25 Citations (Scopus)

Abstract

A number of bicyclic chiral sultams were synthesized based on 1,3-dipolar cycloaddition reactions of nitrile oxides and nitrones with prop-1-ene-1,3- sultone. The corresponding N-enoyl sultams were prepared by acylation. Their relative effectiveness as new chiral auxiliaries in asymmetric synthesis was evaluated for the asymmetric Diels-Alder reactions with cyclopentadiene. Good chemical yield and excellent endo selectivity were observed. The relationship between the structure and their effectiveness in promoting asymmetric induction of the synthetic chiral sultams was investigated.

Original language	English
Pages (from-to)	761-771
Number of pages	11
Journal	Tetrahedron Asymmetry
Volume	16
Issue number	4
DOIs	https://doi.org/10.1016/j.tetasy.2004.12.026
Publication status	Published - 21 Feb 2005

Scopus Subject Areas

Catalysis
Physical and Theoretical Chemistry
Organic Chemistry
Inorganic Chemistry

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10.1016/j.tetasy.2004.12.026

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title = "Synthesis of chiral sultams and their application as chiral auxiliaries in an asymmetric Diels-Alder reaction",

abstract = "A number of bicyclic chiral sultams were synthesized based on 1,3-dipolar cycloaddition reactions of nitrile oxides and nitrones with prop-1-ene-1,3- sultone. The corresponding N-enoyl sultams were prepared by acylation. Their relative effectiveness as new chiral auxiliaries in asymmetric synthesis was evaluated for the asymmetric Diels-Alder reactions with cyclopentadiene. Good chemical yield and excellent endo selectivity were observed. The relationship between the structure and their effectiveness in promoting asymmetric induction of the synthetic chiral sultams was investigated.",

author = "Zhang, {Hong Kui} and Chan, {Wing Hong} and Lee, {Albert W. M.} and Wong, {Wai Yeung} and Xia, {Ping Fang}",

note = "Funding Information: The work described in the paper was fully supported by grants from the University Grants Committee of the Hong Kong Special Administrative Region, China (AOE/p-10/01 and HKBU 2024/OOP) and a grant from the Hong Kong Baptist University (PRG/01-02/II-41). Publisher copyright: {\textcopyright} 2005 Elsevier Ltd. All rights reserved.",

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doi = "10.1016/j.tetasy.2004.12.026",

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T1 - Synthesis of chiral sultams and their application as chiral auxiliaries in an asymmetric Diels-Alder reaction

AU - Zhang, Hong Kui

AU - Chan, Wing Hong

AU - Lee, Albert W. M.

AU - Wong, Wai Yeung

AU - Xia, Ping Fang

N1 - Funding Information: The work described in the paper was fully supported by grants from the University Grants Committee of the Hong Kong Special Administrative Region, China (AOE/p-10/01 and HKBU 2024/OOP) and a grant from the Hong Kong Baptist University (PRG/01-02/II-41). Publisher copyright: © 2005 Elsevier Ltd. All rights reserved.

PY - 2005/2/21

Y1 - 2005/2/21

N2 - A number of bicyclic chiral sultams were synthesized based on 1,3-dipolar cycloaddition reactions of nitrile oxides and nitrones with prop-1-ene-1,3- sultone. The corresponding N-enoyl sultams were prepared by acylation. Their relative effectiveness as new chiral auxiliaries in asymmetric synthesis was evaluated for the asymmetric Diels-Alder reactions with cyclopentadiene. Good chemical yield and excellent endo selectivity were observed. The relationship between the structure and their effectiveness in promoting asymmetric induction of the synthetic chiral sultams was investigated.

AB - A number of bicyclic chiral sultams were synthesized based on 1,3-dipolar cycloaddition reactions of nitrile oxides and nitrones with prop-1-ene-1,3- sultone. The corresponding N-enoyl sultams were prepared by acylation. Their relative effectiveness as new chiral auxiliaries in asymmetric synthesis was evaluated for the asymmetric Diels-Alder reactions with cyclopentadiene. Good chemical yield and excellent endo selectivity were observed. The relationship between the structure and their effectiveness in promoting asymmetric induction of the synthetic chiral sultams was investigated.

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U2 - 10.1016/j.tetasy.2004.12.026

DO - 10.1016/j.tetasy.2004.12.026

M3 - Journal article

AN - SCOPUS:13844294140

SN - 0957-4166

VL - 16

SP - 761

EP - 771

JO - Tetrahedron Asymmetry

JF - Tetrahedron Asymmetry

IS - 4

ER -

Synthesis of chiral sultams and their application as chiral auxiliaries in an asymmetric Diels-Alder reaction

Abstract

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