Iterative Synthesis of Oligo-1,4-diols via Catalytic Anti-Markovnikov Hydration of Terminal Alkynes

Thomas Kribber; Aurélie Labonne; Lukas Hintermann

doi:10.1055/s-2007-983884

PAPER

Iterative Synthesis of Oligo-1,4-diols via Catalytic Anti-Markovnikov Hydration of Terminal Alkynes

Thomas Kribber, Aurélie Labonne, Lukas Hintermann*
Institut für Organische Chemie, RWTH Aachen, Landoltweg 1, 52074 Aachen, Germany
e-Mail: lukas.hintermann@oc.rwth-aachen.de;

Abstract

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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.

Key words

addition reactions - aldehydes - alkynes - homogeneous catalysis - ruthenium

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