Synthesis of a Six-Membered-Ring (2R)-10a-Homobornane-10a,2-sultam and Structural Comparison with Oppolzer's, Lang's, and King's Sultams

✍ Scribed by Anna Piątek; Christian Chapuis; Janusz Jurczak

• Publisher: John Wiley and Sons
• Year: 2002
• Tongue: German
• Weight: 230 KB
• Volume: 85
• Category: Article
• ISSN: 0018-019X
• DOI: 10.1002/1522-2675(200207)85:7<1973::aid-hlca1973>3.0.co;2-n

✦ Synopsis

The new six-membered-ring (2R)-10a-homobornane-10a,2-sultam (À)-3a was synthesized and its X-ray structural analysis was compared with that of the novel structure of the five-membered-ring (2R)-bornane-10,2sultam analogues (À)-1a,b as well as with that already published for the six-membered-ring trans-decalin-like sultam 4a. Based on DN** density-function calculations and X-ray crystallographic studies of the N-methylated analogues (À)-1e and 4b and by comparing with the conformation of the N-fluoro derivatives (À)-1c and ()-1d, the anomeric stabilization was estimated to be smaller than the 2.0 ± 2.5 kcal/mol earlier suggested. The direction of pyramidalization is rationalized in terms of H-bond and steric and electronic interactions and extended to the known toluenesultam derivatives 10a ± c.