A one-step synthesis of 2,3-dihydro-4H-pyran-4-ones from 3-ethoxy alpha,beta-unsaturated lactones.
[reaction: see text] Addition of diverse nucleophiles to the unsaturated lactone 2 that results from hetero Diels-Alder reaction of Brassard's diene 1 with aldehydes leads to an efficient and general approach to the synthesis of 2,3-dihydro-4H-pyran-4-ones 3.
Winkler
Jeffrey D
JD
Department of Chemistry, The University of Pennsylvania, Philadelphia, Pennsylvania 19104, USA. winkler@sas.upenn.edu
Oh
Kyungsoo
K
D007783:Lactones / Q000737:chemistry*; D015394:Molecular Structure; D011753:Pyrones / Q000138:chemical synthesis*; D013237:Stereoisomerism
D007783:Lactones; D011753:Pyrones