Helical primary structures of four-membered rings: (M)-trispiro[3.0.0.3.2.2]tridecane

✍ Scribed by Lutz Fitjer; Ralf Gerke; Jörg Weiser; Gabor Bunkoczi; Judit E Debreczeni

• Book ID: 104205317
• Publisher: Elsevier Science
• Year: 2003
• Tongue: French
• Weight: 298 KB
• Volume: 59
• Category: Article
• ISSN: 0040-4020
• DOI: 10.1016/s0040-4020(03)00617-3

✦ Synopsis

The synthesis of (M)-trispiro[3.0.0.3.2.2]tridecane [(M)-4], the first hydrocarbon with a helical primary structure of fourmembered rings, is described. Key step is the kinetic resolution of a cyclobutanone through reduction with bakers' yeast. As compared to its analogue of three-membered rings, (M)-trispiro[2.0.0.2.1.1]nonane [(M)-1], the specific rotation of (M)-4 is cut in three. According to molecular mechanics calculations this could be due to a potential to adopt different conformations, not given in (M)-1, and to the fact, that (M)-4 describes a distinctly shorter section of a helix than (M)-1.