4.7 Article

A Strategy to Synthesize Taxol Side Chain and (-)-epi Cytoxazone via Chiral Bronsted Acid-Rh2(OAc)4 Co-catalyzed Enantioselective Three-Component Reactions

Journal

JOURNAL OF ORGANIC CHEMISTRY
Volume 75, Issue 21, Pages 7483-7486

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/jo101559p

Keywords

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Funding

  1. National Science Foundation of China [20932003]
  2. MOST of China [2009ZX09501-017]
  3. [09JC1404901]
  4. [09ZZ45]

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A new approach to synthesize optically active beta-amino-alpha-hydroxyl acid derivatives via chiral Bronsted (OAc)(4) cocatalyzed three-component reactions of diazo acetates with alcohols and imines is reported. A matched reaction system was identified to give the products in moderate diastereoselectivity and good enantioselectivity. Application of this methodology is demonstrated in the efficient synthesis of a taxol side chain and (-)-epi-cytoxazone.

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