Synthesis, isomerisation and diels-alder reactions of (5 S)-5-phenyl-3,4-dehydromorpholin-2-one

(5 S)-5-Phenyl-3,4-dehydromorpholin-2-one [(5 S)-5-phenyl-5,6-dihydro-2 H-1,4-oxazin-2-one] 2a is prepared by a one-pot bromination / dehydrobromination of (5 S)-5-phenyl morpholin-2-one and undergoes regio- and diastereocontrolled catalysed Diels-Alder reactions. Title compound 2a is synthesised by...

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Bibliographic Details
Published in:Tetrahedron: asymmetry 1996-09, Vol.7 (9), p.2563-2566
Main Authors: Ager, David, Cooper, Nicholas, Cox, Geoffrey G., Garro-Hélion, Florence, Harwood, Laurence M.
Format: Article
Language:English
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Summary:(5 S)-5-Phenyl-3,4-dehydromorpholin-2-one [(5 S)-5-phenyl-5,6-dihydro-2 H-1,4-oxazin-2-one] 2a is prepared by a one-pot bromination / dehydrobromination of (5 S)-5-phenyl morpholin-2-one and undergoes regio- and diastereocontrolled catalysed Diels-Alder reactions. Title compound 2a is synthesised by one-pot bromination / dehydrobromination of (5 S)-5-phenylmorpholin-2-one. Reaction of 2a with triethylamine gives isomeric 5-phenyl-4,5-didehydromorpholin-2-one. 2a Undergoes regio- and diastereoselective Diels-Alder reactions.
ISSN:0957-4166
1362-511X
DOI:10.1016/0957-4166(96)00329-1