An Intramolecular 1,3-Dipolar Cycloaddition Involving One Alkyne and Two Nitrone Groups

✍ Scribed by Aurich, Hans Günter ;Biesemeier, Frank ;Harms, Klaus

• Book ID: 102365956
• Publisher: John Wiley and Sons
• Year: 1997
• Tongue: English
• Weight: 317 KB
• Volume: 1997
• Category: Article
• ISSN: 0947-3440
• DOI: 10.1002/jlac.199719970306

✦ Synopsis

Abstract

The chiral nonracemic compound 4 was prepared from ethyl (S)‐(–)‐lactate and 1,4‐dibromo‐2‐butyne. Reduction with DIBAH at −72°C and subsequent treatment of the resulting dialdehyde with N‐methylhydroxylamine yielded the dinitrone 5, which underwent two consecutive intramolecular cycloadditions to give the chiral nonracemic compound 7. The structure of 7 was confirmed by an X‐ray analysis. Reductive ring opening afforded compound 8.