L. Harwood, I. A. Lilley
Jan 15, 1993
Citations
0
Influential Citations
31
Citations
Journal
Tetrahedron Letters
Abstract
Abstract Aldehydes possessing unsaturation at C-5 or C-6 condense with (5 S )-phenylmorpholin-2-one ( 1 ), generating chiral stabilised azomethine ylids which undergo concommitant diastereospecific intramolecular 3+2 dipolar cycloaddition to furnish adducts ( 2 ), ( 4 ), and ( 5 ) which may be converted to homochiral bicyclic proline derivatives. Reductive desulfurisation of the thioether derivative ( 5 ) leads to (2 S ,4 R ,5 R )-4,5-dimethylproline ( 7 ).