4.6 Article

Catalyst-Directed Diastereo- and Site-Selectivity in Successive Nucleophilic and Electrophilic Allylations of Chiral 1,3-Diols: Protecting-Group-Free Synthesis of Substituted Pyrans

Journal

CHEMISTRY-A EUROPEAN JOURNAL
Volume 20, Issue 41, Pages 13382-13389

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201404065

Keywords

catalyst directed diasteroselectivity; polyketides; protecting group-free reactions; pyran; transfer hydrogenation

Funding

  1. Robert A. Welch Foundation [F-0038]
  2. NIH-NIGMS [RO1-GM093905]

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The iridium-catalyzed, protecting group-free synthesis of 4-hydroxy-2,6-cis- or trans-pyrans through successive nucleophilic and electrophilic allylations of chiral 1,3diols occurs with complete levels of catalyst-directed diastereoselectivity in the absence of protecting groups, premetallated reagents, or discrete alcohol-to-aldehyde redox reactions.

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