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Synfacts 2008(7): 0734-0734  
DOI: 10.1055/s-2008-1078460
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York

Synthesis of 1,5-Hexadienes via a Retro-Allylation/Allylation Protocol

Contributor(s): Mark Lautens, Frédéric Ménard
Y. Sumida, S. Hayashi, K. Hirano, H. Yorimitsu*, K. Oshima*
Kyoto University, Japan
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Publikationsdatum:
20. Juni 2008 (online)

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Significance

Nickel catalysis allowed the coupling of two simple allyl moieties, one electrophilic and the other nucleophilic, to prepare 1,5-dienes 3, 5, or 7 with exceptional regioselectivity. Although palladium has been used previously for this reaction (see Review below), it often leads to b-hydride elimination products if the allylmetal is not preformed. The Ni-catalyzed process brings a solution to this problem.

Review: E. Negishi, B. Liao Handbook of Organopalladium Chemistry for Organic Synthesis; Wiley: New York, 2002.