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

Nongnuch Sutivisedsak, Surendra Dawadi, Christopher D Spilling

Tetrahedron Lett. 2015 Jun 3;56(23):3534-3537.

PMID: 26236053

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.

Chemicals Related in the Paper:

Catalog Number Product Name Structure CAS Number Price
AP205131813 PSS-Allyl-Heptacyclopentyl substituted PSS-Allyl-Heptacyclopentyl substituted 205131-81-3 Price
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