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

Inji Shin, Gang Wang, Michael J. Krische

Research output: Contribution to journalArticlepeer-review

56 Scopus citations

Abstract

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

Original languageEnglish
Pages (from-to)13382-13389
Number of pages8
JournalChemistry - A European Journal
Volume20
Issue number41
DOIs
StatePublished - 1 Oct 2014

Keywords

  • catalyst-directed diastereoselectivity
  • polyketides
  • protecting group-free reactions
  • pyran
  • transfer hydrogenation

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