An unexpected photoadduct of N-carbomethoxymethylpyrrolidine with a chiral butenolide and benzophenone: X-ray structure and synthetic utility

de Alvarenga, E. S., Cardin, C. ORCID: https://orcid.org/0000-0002-2556-9995 and Mann, J. (1997) An unexpected photoadduct of N-carbomethoxymethylpyrrolidine with a chiral butenolide and benzophenone: X-ray structure and synthetic utility. Tetrahedron, 53 (4). pp. 1457-1466. ISSN 0040-4020 doi: 10.1016/S0040-4020(96)01057-5

Abstract/Summary

The regio- and stereoselective photoinduced addition of N-carbomethoxymethylpyrrolidine to 5(S)-tert-butyldimethylsiloxymethyl-furan-2(5H)-one in the presence of benzophenone yields 3(R)-[N-(diphenylhydroxymethyl)carbo methoxymethylpyrrolidin-2′-yl]-4(S)-tert-butyldimethylsiloxymethyl)-butan-4-olides (epimeric at C-2′), and we report the X-ray structure of the major adduct together with its conversion into the 1-azabicyclo[4.3.0]-nonane ring system.