123002-57-3Relevant academic research and scientific papers
Iterative synthesis of oligo-1,4-diols via catalytic anti-Markovnikov hydration of terminal alkynes
Kribber, Thomas,Labonne, Aurelie,Hintermann, Lukas
, p. 2809 - 2818 (2007)
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 r
A Sequential Homologation of Alkynes and Aldehydes for Chain Elongation with Optional 13C-Labeling
Brunner, Andreas,Hintermann, Lukas
supporting information, p. 2787 - 2792 (2016/02/27)
Terminal alkynes (RCCH) are homologated by a sequence of ruthenium-catalyzed anti-Markovnikov hydration of alkyne to aldehyde (RCH2CHO), followed by Bestmann-Ohira alkynylation of aldehyde to chain-elongated alkyne (RCH2CCH). Inverting the sequence by starting from aldehyde brings about the reciprocal homologation of aldehydes instead. The use of 13C-labeled Bestmann-Ohira reagent (dimethyl ((1-13C)-1-diazo-2-oxopropyl)phosphonate) for alkynylation provides straightforward access to singly or, through additional homologation, multiply 13C-labeled alkynes. The labeled alkynes serve as synthetic platform for accessing a multitude of specifically 13C-labeled products. Terminal alkynes with one or two 13C-labels in the alkyne unit have been submitted to alkyne-azide click reactions; the copper-catalyzed version (CuAAC) was found to display a regioselectivity of >50 000:1 for the 1,4- over the 1,5-triazine isomer, as shown analytically by 13C NMR spectroscopy.
