Asymmetric 1,3-Dipolar Cycloaddition of Chiral α, β-Unsaturated-γ-Sultams with Nitrile Oxides and Nitrones

H. Zhang; W. H. Chan; Albert W M Lee; P.-F. Xia; W. Y. Wong

doi:10.2174/1570178043488644

Asymmetric 1,3-Dipolar Cycloaddition of Chiral α, β-Unsaturated-γ-Sultams with Nitrile Oxides and Nitrones

H. Zhang, W. H. Chan, Albert W M Lee, P.-F. Xia, W. Y. Wong

Department of Chemistry

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

Abstract

The scope and limitations of 1,3-dipolar cycloaddition reactions between nitrile oxides and chiral α,β-unsaturated-γ-sultams 2a and 2b have been investigated. Only very marginal diastereoselectivity was observed for the reaction. In contrast, using double asymmetric induction strategy, the cycloaddition products from 2a and chiral nitrones were obtained in better diastereomeric ratios (up to 7.1:1).

Original language	English
Pages (from-to)	63-66
Number of pages	4
Journal	Letters in Organic Chemistry
Volume	1
Issue number	1
DOIs	https://doi.org/10.2174/1570178043488644
Publication status	Published - Jan 2004

User-Defined Keywords

dipolar
cycloaddition
chiral sultams
nitrile oxides
nitrones

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title = "Asymmetric 1,3-Dipolar Cycloaddition of Chiral α, β-Unsaturated-γ-Sultams with Nitrile Oxides and Nitrones",

abstract = "The scope and limitations of 1,3-dipolar cycloaddition reactions between nitrile oxides and chiral α,β-unsaturated-γ-sultams 2a and 2b have been investigated. Only very marginal diastereoselectivity was observed for the reaction. In contrast, using double asymmetric induction strategy, the cycloaddition products from 2a and chiral nitrones were obtained in better diastereomeric ratios (up to 7.1:1).",

keywords = "dipolar, cycloaddition, chiral sultams, nitrile oxides, nitrones",

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

note = "Financial support from the Faculty Research Committee of the Hong Kong Baptist University (FRG/01-02/II-41), the Research Grant Council (HKBU 2024/00P) and the AoE scheme of the UGC (AoE/P-10/01) of the HKSAR is gratefully acknowledged.",

year = "2004",

month = jan,

doi = "10.2174/1570178043488644",

language = "English",

volume = "1",

pages = "63--66",

journal = "Letters in Organic Chemistry",

issn = "1570-1786",

publisher = "Bentham Science Publishers B.V.",

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TY - JOUR

T1 - Asymmetric 1,3-Dipolar Cycloaddition of Chiral α, β-Unsaturated-γ-Sultams with Nitrile Oxides and Nitrones

AU - Zhang, H.

AU - Chan, W. H.

AU - Lee, Albert W M

AU - Xia, P.-F.

AU - Wong, W. Y.

N1 - Financial support from the Faculty Research Committee of the Hong Kong Baptist University (FRG/01-02/II-41), the Research Grant Council (HKBU 2024/00P) and the AoE scheme of the UGC (AoE/P-10/01) of the HKSAR is gratefully acknowledged.

PY - 2004/1

Y1 - 2004/1

N2 - The scope and limitations of 1,3-dipolar cycloaddition reactions between nitrile oxides and chiral α,β-unsaturated-γ-sultams 2a and 2b have been investigated. Only very marginal diastereoselectivity was observed for the reaction. In contrast, using double asymmetric induction strategy, the cycloaddition products from 2a and chiral nitrones were obtained in better diastereomeric ratios (up to 7.1:1).

AB - The scope and limitations of 1,3-dipolar cycloaddition reactions between nitrile oxides and chiral α,β-unsaturated-γ-sultams 2a and 2b have been investigated. Only very marginal diastereoselectivity was observed for the reaction. In contrast, using double asymmetric induction strategy, the cycloaddition products from 2a and chiral nitrones were obtained in better diastereomeric ratios (up to 7.1:1).

KW - dipolar

KW - cycloaddition

KW - chiral sultams

KW - nitrile oxides

KW - nitrones

U2 - 10.2174/1570178043488644

DO - 10.2174/1570178043488644

M3 - Journal article

SN - 1570-1786

VL - 1

SP - 63

EP - 66

JO - Letters in Organic Chemistry

JF - Letters in Organic Chemistry

IS - 1

ER -

Asymmetric 1,3-Dipolar Cycloaddition of Chiral α, β-Unsaturated-γ-Sultams with Nitrile Oxides and Nitrones

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