L. Harwood, L. C. Kitchen
Oct 8, 1993
Citations
0
Influential Citations
15
Citations
Journal
Tetrahedron Letters
Abstract
Abstract Due to the steric contraints imposed upon the bridging chain by the three-carbon linear unit associated with the alkyne, hex-5-ynal condenses with (5 R )-phenylmorpholin-2-one ( 1 ), and undergoes intramolecular 3+2 dipolar cycloaddition via the syn - azomethine ylid to furnish adduct ( 2 ). This is in contrast to the anti -ylid pathway exhibited by the ylid derived from ( 1 ) and hept-6-ynal, which fumishes ( 6 ); or similar reactions involving alkene dipolarophilic moieties.