Exo Diastereoselective Diels-Alder Reactions of (R)-2-Phenyl-4-Methylene-Oxazolidin-5-one

S.G. Pyne, J. Safaei, D.C.R. Hockless, Brian Skelton, A.N. Sobolev, Allan White

Research output: Contribution to journalArticle

30 Citations (Scopus)

Abstract

The thermally induced Diels-Alder reactions of (R)-2-phenyl-4-methylene-oxazolidin-5-one 2 and substituted 1,3-cyclohexadienes and substituted Ig-butadienes gives exo diastereomeric Diels-Alder adducts. In some cases the initially formed adducts undergo epimerization at the amino-acetal carbon, however the stereochemical integrity of the quaternary alpha-amino acid stereogenic centre is maintained and Diels-Alder adducts can be obtained in high enantiomeric purity (> 90% eel. The stereochemistry of these adducts has been elucidated by single crystal X-ray structure determinations and 2D H-1 NMR analysis.
Original languageEnglish
Pages (from-to)941-956
JournalTetrahedron
Volume50
Issue number3
DOIs
Publication statusPublished - 1994

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