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1,3-Dipolar cycloadditions of prop-1-ene-1,3-sultone with nitrile oxides/nitrones

✍ Scribed by H. Zhang; W.H. Chan; Albert W.M. Lee; W.Y. Wong

Publisher
Elsevier Science
Year
2003
Tongue
French
Weight
142 KB
Volume
44
Category
Article
ISSN
0040-4039

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✦ Synopsis

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.

πŸ“œ SIMILAR VOLUMES

1,3-dipolar cycloaddition reactions of n
1,3-dipolar cycloaddition reactions of nitrile oxides to prop-1-ene-1,3-sultone
✍ Li Tian; Guo-Yan Xu; Yong Ye; Lun-Zu Liu πŸ“‚ Article πŸ“… 2003 πŸ› Journal of Heterocyclic Chemistry 🌐 English βš– 91 KB

## Abstract The reaction of prop‐1‐ene‐1,3‐sultone **1** with a variety of nitrile oxides **3** afforded novel [3+2] cycloaddition products **4** in good yield. The cycloaddition reaction achieved excellent regioselectivity.