Iterative synthesis of oligo-1,4-diols via catalytic anti-Markovnikov hydration of terminal alkynes

Thomas Kribber, Aurélie Labonne, Lukas Hintermann

Research output: Contribution to journalArticlepeer-review

32 Scopus citations

Abstract

A sequential, iterative synthesis of oligo-1,4-diol building blocks has been realized via (a) propargylation of an aldehyde with allenylzinc bromide, (b) alcohol protection and (c) ruthenium-catalyzed anti-Markovnikov hydration of the terminal alkyne to release an aldehyde for the next iteration. Linear chains with 1,4-, 1,4,7- 1,4,7,10- and 1,4,7,10,13- functionalization patterns have been obtained by consecutive sequential iterations.

Original languageEnglish
Pages (from-to)2809-2818
Number of pages10
JournalSynthesis
Issue number18
DOIs
StatePublished - 17 Sep 2007
Externally publishedYes

Keywords

  • Addition reactions
  • Aldehydes
  • Alkynes
  • Homogeneous catalysis
  • Ruthenium

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