Syntheses of 2,5-disubstituted dihydrofurans from gamma-substituted chiral allenamides.
[reaction: see text] Details of a synthesis of dihydrofurans using gamma-substituted chiral allenamides are described here. Some transformations of these dihydrofurans are also examined including a highly stereoselective dihydroxylation and a rare account of a Lewis acid-mediated removal of an N-acyl substituent at the anomeric carbon of a tetrahydrofuran ring system. These studies provide further support for the synthetic utility of allenamides.
Berry
Craig R
CR
Department of Chemistry, University of Minnesota, Minneapolis, Minnesota 55455, USA.
Hsung
Richard P
RP
Antoline
Jennifer E
JE
Petersen
Matthew E
ME
Challeppan
Rameshkumar
R
Nielson
Jessica A
JA