Dimethyl Acetylenedicarboxylate

Stelmach, John E.; Winkler, Jeffrey D.

doi:10.1002/047084289x.rd295

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2014

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“…Esters of acetylene dicarboxylic acid and especially dimethyl acetylenedicarboxylate (DMAD, 1a ) are highly versatile tools for organic chemists [1,2,3,4,5,6,7]. These compounds are successfully utilized as dienophiles in Diels–Alder reactions, as dipolarophiles in 1,3-dipolar cycloadditions and also as components in [2 + 2] or other cycloaddition reactions.…”

Section: Introductionmentioning

confidence: 99%

Synthesis with Perfect Atom Economy: Generation of Furan Derivatives by 1,3-Dipolar Cycloaddition of Acetylenedicarboxylates at Cyclooctynes

et al. 2014

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Cyclooctyne and cycloocten-5-yne undergo, at room temperature, a 1,3-dipolar cycloaddition with dialkyl acetylenedicarboxylates 1a,b to generate furan-derived short-lived intermediates 2, which can be trapped by two additional equivalents of 1a,b or alternatively by methanol, phenol, water or aldehydes to yield polycyclic products 3b-d, orthoesters 4a-c, ketones 5 or epoxides 6a,b, respectively. Treatment of bis(trimethylsilyl) acetylenedicarboxylate (1c) with cyclooctyne leads to the ketone 7 via retro-Brook rearrangement of the dipolar intermediate 2c. In all cases, the products are formed with perfect atom economy.

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Section: Introductionmentioning

confidence: 99%