4.8 Article

Formal [4+1]-Cycloaddition of Homopropargyl Alcohols to Diazo Dicarbonyl Compounds Giving Substituted Tetrahydrofurans

Journal

ORGANIC LETTERS
Volume 16, Issue 3, Pages 1004-1007

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/ol403746r

Keywords

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Funding

  1. JSPS [22249001, 25460017, 21790019]
  2. MEXT [2105, 22106538, 24106736]
  3. Naito Foundation
  4. Grants-in-Aid for Scientific Research [25253002, 25460017, 22106538, 24105526, 24659009, 21790019, 24106736] Funding Source: KAKEN

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A novel formal [4 + 1]-cycloaddition of readily available homopropargyl alcohols with diazo dicarbonyl compounds is described, which involves tandem O-H insertion/Conia-ene cyclization under cooperative Rh(II)/Zn(II) catalysis. This reaction provides easy access to various substituted tetrahydrofurans and exhibits complete E-selectivity in the case of nonterminal alkynes.

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