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Paper | Special issue | Vol 74, No. 1, 2007, pp.473-489
Published online, 30th October, 2007
DOI: 10.3987/COM-07-S(W)67
Palladium-Catalyzed Domino-Wacker-Carbonylation Reaction for the Enantioselective Synthesis of Chromans and Benzodioxins

Lutz F. Tietze,* Julia Zinngrebe, Dirk A. Spiegl, and Florian Stecker

*Institute of Organic and Biomolecular Chemistry, Georg-August-University, Tammannstr. 2, D-37077 Göttingen, Germany

Abstract

A palladium-catalyzed domino reaction for the formation of chromans 9 as well as 10 and benzodioxines 13 is described starting from the alkenes 6 as well as 8 and the allyl phenyl ethers 12. The domino reaction comprises an enantioselective intramolecular Wacker oxidation, a subsequent CO-insertion and a nucleophilic substitution of the intermediately formed palladium-species.