Syntheses of 2,5-disubstituted dihydrofurans from gamma-substituted chiral allenamides |
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Authors: | Berry Craig R Hsung Richard P Antoline Jennifer E Petersen Matthew E Challeppan Rameshkumar Nielson Jessica A |
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Institution: | Department of Chemistry, University of Minnesota, Minneapolis, Minnesota 55455, USA. |
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Abstract: | 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. |
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