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

ISSN: 1570-1786
E-ISSN: 1875-6255

Asymmetric 1,3-Dipolar Cycloaddition of Chiral α, β-Unsaturated-γ-Sultams with Nitrile Oxides and Nitrones
Authors: H. Zhang¹, W. H. Chan², Albert W.M. Lee³, P.- F. Xia⁴ and W. Y. Wong⁵
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¹ Department of Chemistry and Central Laboratory of the Institute of Molecular Technology for Drug Discovery and Synthesis, Hong Kong Baptist University, Kowloon Tong, Hong Kong SAR. ² Department of Chemistry and Central Laboratory of the Institute of Molecular Technology for Drug Discovery and Synthesis, Hong Kong Baptist University, Kowloon Tong, Hong Kong SAR. ³ Department of Chemistry and Central Laboratory of the Institute of Molecular Technology for Drug Discovery and Synthesis, Hong Kong Baptist University, Kowloon Tong, Hong Kong SAR. ⁴ Department of Chemistry and Central Laboratory of the Institute of Molecular Technology for Drug Discovery and Synthesis, Hong Kong Baptist University, Kowloon Tong, Hong Kong SAR. ⁵ Department of Chemistry and Central Laboratory of the Institute of Molecular Technology for Drug Discovery and Synthesis, Hong Kong Baptist University, Kowloon Tong, Hong Kong SAR.
Source: Letters in Organic Chemistry, Volume 1, Issue 1, Jan 2004, p. 63 - 66
DOI: https://doi.org/10.2174/1570178043488644
- Available online: 01 Jan 2004

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).

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2004-01-01

2025-10-03

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Article Type: Review Article

Keyword(s): chiral sultams; cycloaddition; dipolar; nitrile oxides; nitrones

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

Abstract

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