Beilstein J. Org. Chem.2014,10, 1365–1371, doi:10.3762/bjoc.10.139
hydroxylation of propargylic malonate 5 without work-up of any intermediate.
Keywords: alkylation; ‘click’ chemistry; ‘clickable’ polylactide; decomposition; diethyl 2-acetamidomalonate; 2-hydroxy-4-pentynoic acid; one-pot; optimization; propargyl bromide; propargyl tosylate; safeandeconomical; Introduction
feasible probably due to the interruption of the ethynyl proton in the presence of organometallic reagents [29].
As discussed above, there are two important factors that should be taken into account in order to achieve a safeandeconomical route resulting in precursor 1: 1) a non-explosive and cheap
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Graphical Abstract
Scheme 1:
Synthesis of 2-hydroxy-4-pentynoic acid (1).
Beilstein J. Org. Chem.2011,7, 897–936, doi:10.3762/bjoc.7.103
flexibility in comparison with the intramolecular strategy and offers a safeandeconomical alternative to those based on diazo substrates.
A catalytic approach to functionalized divinyl ketones through a gold-catalyzed rearrangement of (3-acyloxyprop-1-ynyl)oxiranes 64 has also been developed [38]. The