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The Optimization Of A One-Pot Heteroconjugate Addition-Oxidation-Diels-Alder Reaction, Christina Vivelo
The Optimization Of A One-Pot Heteroconjugate Addition-Oxidation-Diels-Alder Reaction, Christina Vivelo
Honors Theses
Ynoate esters are ideal reagents for one-pot reactions due to their ability to undergo multiple addition reactions in one flask. Ethyl propiolate undergoes a heteroconjugate addition reaction with aromatic thiol nucleophiles, producing an enoate which is then oxidized by m-CPBA and is able to undergo a Diels–Alder reaction with cyclopentadiene. The work presents the optimization of a three-step heteroconjugate addition-oxidation-Diels–Alder reaction to yield cyclic compounds favoring endo stereochemistry, which may be used in further synthesis of biologically active compounds such as (+)-Methyl-5-epi-Shikimate or Deipeptyl-IV-Peptidase inhibitor.