1,3-Dipolar cycloadditions of prop-1-ene-1,3-sultone with nitrile oxides/nitrones |
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| Authors: | H. ZhangW.H. Chan Albert W.M. LeeW.Y. Wong |
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| Affiliation: | Department of Chemistry and Central Laboratory of the Institute of Molecular Technology for Drug Discovery and Synthesis, Hong Kong Baptist University, Kowloon Tong, Kowloon, Hong Kong SAR |
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| 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. |
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