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Trapping Hemiacetals with Phosphono Substituted Palladium ?-Allyl Complexes for the Synthesis of Substituted Cyclic Ethers.

ABSTRACT: Oxidation of hydroxy substituted phosphono allylic carbonates gave the aldehyde substituted phosphonates in good yield. Stereospecific palladium (0)-catalyzed cyclization in the presence of methanol or water gave acetal tetrahydrofuran and tetrahydropyran vinyl phosphonate products derived from hemiacetal trapping. The tetrahydrofuran acetals undergo Lewis acid catalyzed addition of nucleophiles to give diastereoisomeric mixtures of substituted tetrahydrofurans.

SUBMITTER: Sutivisedsak N 

PROVIDER: S-EPMC4518476 | biostudies-literature | 2015 Jun

REPOSITORIES: biostudies-literature

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Trapping Hemiacetals with Phosphono Substituted Palladium π-Allyl Complexes for the Synthesis of Substituted Cyclic Ethers.

Sutivisedsak Nongnuch N   Dawadi Surendra S   Spilling Christopher D CD  

Tetrahedron letters 20150601 23

Oxidation of hydroxy substituted phosphono allylic carbonates gave the aldehyde substituted phosphonates in good yield. Stereospecific palladium (0)-catalyzed cyclization in the presence of methanol or water gave acetal tetrahydrofuran and tetrahydropyran vinyl phosphonate products derived from hemiacetal trapping. The tetrahydrofuran acetals undergo Lewis acid catalyzed addition of nucleophiles to give diastereoisomeric mixtures of substituted tetrahydrofurans. ...[more]

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