Direct and stereospecific synthesis of allenes via reduction of propargylic alcohols with Cp2Zr(H)Cl

Xiaotao Pu, Joseph M. Ready

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Abstract

Allenes can be synthesized via the direct SN2′ addition of hydride to propargylic alcohols. Previous examples of this approach, however, have involved harsh reaction conditions and have suffered from incomplete transfer of central chirality to axial chirality. Here we show that Cp2Zr(H)Cl can react with the zinc or magnesium alkoxides of propargylic alcohols to generate allenes in good yield and in high optical purity. Dialkyl-, alkyl-aryl-, and diaryl-allenes are accessible by this method. Furthermore, the reaction can provide silyl-substituted allenes, trisubstituted allenes, and terminal allenes.

Original languageEnglish (US)
Pages (from-to)10874-10875
Number of pages2
JournalJournal of the American Chemical Society
Volume130
Issue number33
DOIs
Publication statusPublished - Aug 20 2008

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ASJC Scopus subject areas

  • Chemistry(all)

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