Photocycloaddition of Six-Membered Cyclic Enones to Propen-2-yl Isocyanate

✍ Scribed by Maryam Bahaji; Paul Margaretha

• Book ID: 102255794
• Publisher: John Wiley and Sons
• Year: 2007
• Tongue: German
• Weight: 75 KB
• Volume: 90
• Category: Article
• ISSN: 0018-019X
• DOI: 10.1002/hlca.200790149

✦ Synopsis

Abstract

On irradiation in the presence of propen‐2‐yl isocyanate (4), six‐membered cyclic enones 3 are converted into regio‐ and stereoisomeric mixtures of [2+2] cycloadducts 5–10; the preferentially formed HT products, 5–8, can be converted into the corresponding bicyclic amines by acid hydrolysis, whereas, under these conditions, the regioisomeric HH‐isocyanato derivatives undergo a retro‐Mannich reaction.