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Palladium(II)-Catalyzed SN2' Reactions of α-Allenic Acetates. Stereoconvergent Synthesis of (Z,E)-2-Bromo-1,3-dienes

Attila Horváth and Jan-E. Bäckvall*

*Department of Organic Chemistry, Arrhenius Laboratory, Stockholm University, SE-106 91, Stockholm, Sweden

A. Horváth, J.-E. Bäckvall, J. Org. Chem., 2001, 66, 8120-8126.

DOI: 10.1021/jo015950x

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Abstract

The reaction of acetylated α-allenic alcohols with LiBr in the presence of 1.5 mol % of Pd(OAc)2 provides substituted (Z,E)-2-bromo-1,3-dienes in good yields with excellent diastereoselectivity. Both secondary and tertiary acetates as well as terminal and nonterminal allenes can be converted.

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Key Words

1,3-Dienes, Bromination

ID: J42-Y2001