Copper-catalyzed synthesis of 2,4-disubstituted allenoates from α-diazoesters.

ABSTRACT: 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.

SUBMITTER: Hassink M 

PROVIDER: S-EPMC3128944 | biostudies-literature | 2011 May

REPOSITORIES: biostudies-literature