April 12, 2011

Copper-Catalyzed Synthesis of 2,4-Disubstituted Allenoates from α-Diazoesters

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Resumen

A Cu-catalyzed method for coupling α-substituted-α-diazoesters with terminal alkynes to give substituted allenoates is described. Key to the development of a selective method was the recognition that an adventitous base catalyzes the isomerization to form the allenoate product. A plausible mechanism is proposed, based in part on evidence against a mechanism that involves a Cu(I)-acetylide as a low-valent intermediate.

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Hassink et al. (Tue,) studied this question.

synapsesocial.com/papers/69fcdef95d981208085090c1 https://doi.org/https://doi.org/10.1021/ol2006242

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