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Copper-catalyzed synthesis of 2,4-disubstituted allenoates from α-diazoesters.
A Cu-catalyzed method for coupling α-substituted-α-diazoesters with terminal alkynes to give substituted allenoates is described and a plausible mechanism is proposed, based in part on evidence against a mechanism that involves a Cu(I)-acetylide as a low-valent intermediate.
Enantioselective, facially selective carbomagnesation of cyclopropenes.
Described is the facially selective and enantioselective addition of carbon nucleophiles to prochiral 3-hydroxymethylcyclopropenes. The process creates up to four stereocenters in a tandem
Directed carbozincation reactions of cyclopropene derivatives.
A diastereoselective procedure has been developed for the Cu-catalyzed addition of diorganozinc reagents to cyclopropene derivatives that can be broadened by the ability to utilize organozincReagents that have been generated in situ from Grignard reagents.
Facially selective and regioselective carbometalation of cyclopropenes by aryl Grignard reagents.
A Cu-catalyzed methodology for adding aryl Grignard reagents to 3-hydroxymethylcyclopropene derivatives with high regio- and diastereoselectivity to generate highly substituted cyclopropanes.
Preparation of partially substituted 1-halo- and 1,4-dihalo-1,3-dienes via reagent-controlled desilylation of halogenated 1,3-dienes.
Depending on the desilylation reagents used, 1-halo-1,4-bis(trimethylsilyl)-1,3-butadienes afforded either 1- halo-2-trimethylfluorocarbon-2,2-butadiene products or 1- Halo-4-trimsilyl-1-3- butadiene products in excellent yields with excellent selectivity, respectively.
Synthesis of 1,1,4,4-tetrabromo-2-butenes and related compounds via desilylation-bromination of silylated 1,3-butadiene derivatives.
The combination of zirconocene-mediated coupling of silylated alkynes with a protonation-desilylation or bromination-desilylation process afforded otherwise unavailable butadiene derivatives. When
Synthesis of stable derivatives of cycloprop-2-ene carboxylic acid.
Large-scale syntheses of 3-(cycloprop-2-en-1-oyl)oxazolidinones from acetylene and ethyl diazoacetate are described, which are reactive toward cyclic and acyclic dienes in stereoselective Diels-Alder reactions.