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Palladium-Catalyzed Propargylic Substitution with Phosphorus Nucleophiles: Efficient, Stereoselective Synthesis of Allenylphosphonates and Related Compounds

Marcin Kalek, Tommy Johansson, Martina Jezowska and Jacek Stawinski*

*Department of Organic Chemistry, Arrhenius Laboratory, Stockholm University, S-106 91 Stockholm, Sweden, Email: jsorgan.su.se

M. Kalek, T. Johansson, M. Jezowska, J. Stawinski, Org. Lett., 2010, 12, 4702-4704.

DOI: 10.1021/ol102121j (free Supporting Information)


Abstract

A new, efficient method based on a palladium(0)-catalyzed reaction of propargylic derivatives with various phosphorus nucleophiles produces allenylphosphonates and their analogues with defined stereochemistry in the allenic and the phosphonate moiety.

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Key Words

Phosphonates, Phosphinates, Allenes


ID: J54-Y2010-2960