147092-33-9Relevant academic research and scientific papers
Exo diastereoselective Diels-Alder reactions of (R)-2-phenyl-4-methylene-oxazolidin-5-one
Pyne,Safaei,Hockless,Skelton,Sobolev,White
, p. 941 - 956 (2007/10/02)
The thermally induced Diels-Alder reactions of (R)-2-phenyl-4-methylene-oxazolidin-5-one 2 and substituted 1,3-cyclohexadienes and substituted 1,3-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 α-amino acid stereogenic centre is maintained and Diels-Alder adducts can be obtained in high enantiomeric purity (>90% ee). The stereochemistry of these adducts has been elucidated by single crystal X-ray structure determinations and 2D 1H NMR analysis.
Asymmetric Synthesis of Chiral Cyclic Amino Acids by Diels-Alder Reactions of (2S)- and (2R)-4-Methyleneoxazolidin-5-ones
Pyne, Stephen G.,Dikic, Branko,Gordon, Peter A.,Skelton, Brian W.,White, Allan H.
, p. 73 - 93 (2007/10/02)
The synthesis of chiral (2S)- and (2R)-4-methyleneoxazolidin-5-ones, in high enantiomeric purity from (S)-S-methylcysteine, and their highly exo-selective Diels-Alder reactions with cyclic dienes are described. (1R,2S,4S)-2-Aminobicycloheptane-2-ca
