Synthesis of enantiopure 3-alkyl-perhydroazepines by diastereoselective 7-endo-radical cyclisation on a chiral 1,3-perhydrobenzoxazine derivative

✍ Scribed by Celia Andrés; Juan P. Duque-Soladana; Jesús M. Iglesias; Rafael Pedrosa

• Publisher: Elsevier Science
• Year: 1999
• Tongue: French
• Weight: 206 KB
• Volume: 40
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(99)00119-7

✦ Synopsis

Competitive alkyl radical 6-exo/7-endo cyclisation on ot, l]-unsaturated amides derived from chiral perhydrobenzoxazines are controlled by the alkene substitution pattern. Stereocontrol leading to 7-endo regioisomers is considerably higher and allows to prepare enantiopure hexahydroazepine derivatives,