Synthesis of Medium-Size Macrocycles by Cinnamate [2 + 2] Photoaddition

✍ Scribed by König, Burkhard ;Leue, Stefanie ;Horn, Clemens ;Caudan, Arnaud ;Desvergne, Jean-Pierre ;Bouas-Laurent, Henri

• Book ID: 102368263
• Publisher: John Wiley and Sons
• Year: 2006
• Tongue: English
• Weight: 253 KB
• Volume: 1996
• Category: Article
• ISSN: 0947-3440
• DOI: 10.1002/jlac.199619960802

✦ Synopsis

Abstract

Unsaturated macrocycles were obtained by [2 + 2] photoaddition of acyclic biscinnamates. The orientation of the chromophores by ortho‐xylyl (2) or aryl‐1,2‐diynyl (6) spacers leads to the formation of photoproducts in solution as single stereoisomers in high yield. The analogous photocyclization of a cis‐enediyne biscinnamate 4 was less efficient, because of a rapid photochemical isomerization of the central double bond.