Unknown

Dataset Information

0

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

ABSTRACT: A Cu-catalyzed method for coupling ?-substituted-?-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

Json Xml
altmetric image

Publications

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

Hassink Matthew M   Liu Xiaozhong X   Fox Joseph M JM  

Organic letters 20110412 9

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. ...[more]

Similar Datasets

Unknown Copper Hydride Catalyzed Enantioselective Synthesis of Axially Chiral 1,3-Disubstituted Allenes.
| S-EPMC6748664 | biostudies-literature
Unknown An Efficient One-Pot Catalyzed Synthesis of 2,4-Disubstituted 5-Nitroimidazoles Displaying Antiparasitic and Antibacterial Activities.
| S-EPMC6152245 | biostudies-literature
Unknown Diastereo- and enantioselective copper catalyzed hydroallylation of disubstituted cyclopropenes.
| S-EPMC6115688 | biostudies-other
Unknown Phosphine-Catalyzed Doubly Stereoconvergent γ-Additions of Racemic Heterocycles to Racemic Allenoates: The Catalytic Enantioselective Synthesis of Protected α,α-Disubstituted α-Amino Acid Derivatives.
| S-EPMC4577964 | biostudies-literature
Unknown Rhodium-catalyzed synthesis of 2,3-disubstituted indoles from β,β-disubstituted stryryl azides.
| S-EPMC3154515 | biostudies-literature
Unknown Copper(I)-catalyzed tandem reaction: synthesis of 1,4-disubstituted 1,2,3-triazoles from alkyl diacyl peroxides, azidotrimethylsilane, and alkynes.
| S-EPMC6278767 | biostudies-literature
Unknown Copper-catalyzed enantioselective synthesis of bridged bicyclic ketals from 1,1-disubstituted-4-methylene-1,6-hexanediols and related alkenols.
| S-EPMC8018521 | biostudies-literature
Unknown Simple two-step synthesis of 2,4-disubstituted pyrroles and 3,5-disubstituted pyrrole-2-carbonitriles from enones.
| S-EPMC3943414 | biostudies-literature
Unknown Copper-Catalyzed Enantio- and Diastereoselective Addition of Silicon Nucleophiles to 3,3-Disubstituted Cyclopropenes.
| S-EPMC6899982 | biostudies-literature
Unknown Rh(II)-Catalyzed Reactions of Diazoesters with Organozinc Reagents.
| S-EPMC4552333 | biostudies-literature