Synthesis of spiropyrrolidines: 1,3-dipolar cycloaddition reactions of an azomethine ylide to unusual dipolarophiles; a molecular orbital study of the cycloaddition reaction

✍ Scribed by A. Amal Raj; R. Raghunathan; E. J. P. Malar

• Publisher: John Wiley and Sons
• Year: 1999
• Tongue: English
• Weight: 312 KB
• Volume: 10
• Category: Article
• ISSN: 1042-7163
• DOI: 10.1002/(sici)1098-1071(1999)10:6<500::aid-hc11>3.0.co;2-m

✦ Synopsis

A simple and efficient method for the synthesis of novel spiropyrrolidines has been accomplished by regioselective 1,3-dipolar cycloaddition reactions of an azomethine ylide generated by thermalring opening of cis-1-cyclohexyl-2-phenyl-3-benzoyl aziridine with various (E)-3-arylidene-4-chromanones. The synthesis proceeds in good yield to afford novel spiropyrrolidines, 1-cyclohexyl-2-phenyl-3-aryl-5-benzoylpyrrolidine-spiro-[4.3Ј]4Ј-chromanones. The X-ray crystal structure analysis of one of the products confirms its structure. Molecular orbital calculations were performed to investigate the regioselectivity of the cycloaddition process.