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Palladium-catalyzed oxaspirocyclizations

Authors
Journal
Tetrahedron
0040-4020
Publisher
Elsevier
Publication Date
Volume
50
Issue
2
Identifiers
DOI: 10.1016/s0040-4020(01)80776-6
Disciplines
  • Chemistry

Abstract

Abstract Palladium-catalyzed oxidation of 1-(3-hydroxyalkyl) and 1-(4-hydroxyalkyl)-1,3-cycloalkadienes results in a stereocontrolled oxaspirocyclization. The reaction proceed via a spirocyclic (π-allyl)palladium intermediate, which is attacked by an acetate or a chloride nucleophile leading to an overall 1,4-addition across the diene. The intermediate (π-allyl) palladium complex was independently prepared and characterized. The stereochemistry of the 1,4-addition can be controlled to give either cis or trans 1,4-addition across the double bonds. The oxaspirocyclization was applied to the total synthesis of theaspirone.

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