Enantioselective synthesis of spiro ethers and spiro ketals via photoaddition of dihydro-4-pyrones to chiral 1, 3-dioxin-4-ones

…, I Rukhman, Z Abramovich

Index: Haddad, Nizar; Rukhman, Igor; Abramovich, Zehavit Journal of Organic Chemistry, 1997 , vol. 62, # 22 p. 7629 - 7636

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Citation Number: 26

Abstract

A versatile and highly stereoselective synthesis of spiro ethers and spiro ketals is presented. The key step in the developed synthetic sequence is based on diastereoselective intramolecular photoaddition of dihydro-4-pyrones to chiral 1, 3-dioxin-4-ones. Subsequent fragmentation of the produced four-membered ring provides spiro ether structures. The spiro ethers can be transformed to their corresponding spiro ketals, with retention of ...