Stereo-and regioselective palladium-catalyzed 1, 4-diacetoxylation of 1, 3-dienes

JE Baeckvall, SE Byström…

Index: Baeckvall, Jan-E.; Bystroem, Styrbjoern E.; Nordberg, Ruth E. Journal of Organic Chemistry, 1984 , vol. 49, # 24 p. 4619 - 4631

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Citation Number: 279

Abstract

Palladium-catalyzed oxidation of 1, 3-dienes in acetic acid using an oxidation system of MnOz and catalytic amounts of p-benzoquinone selectively gives 1, 4-diacetoxy-2-alkenes. The reaction proceeds with high stereoand regioselectivity, and by ligand control the reaction can be made to take place with either cis or trans 1, 4-diacetoxylation across the diene in cyclic systems. Also in an acyclic system the 1, 4-relative stereochemistry can be ...