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

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-oli...

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Bibliographic Details
Published inTetrahedron Vol. 53; no. 4; pp. 1457 - 1466
Main Authors Alvarenga, Elson Santiago de, Cardin, Christine J., Mann, John
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 27.01.1997
Elsevier
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
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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. Graphic
ISSN:0040-4020
1464-5416
DOI:10.1016/S0040-4020(96)01057-5