78932-45-3Relevant articles and documents
Selective carbene transfer to amines and olefins catalyzed by ruthenium phthalocyanine complexes with donor substituents
Cailler, Lucie P.,Kroitor, Andrey P.,Martynov, Alexander G.,Gorbunova, Yulia G.,Sorokin, Alexander B.
supporting information, p. 2023 - 2031 (2021/02/26)
Electron-rich ruthenium phthalocyanine complexes were evaluated in carbene transfer reactions from ethyl diazoacetate (EDA) to aromatic and aliphatic olefins as well as to a wide range of aromatic, heterocyclic and aliphatic amines for the first time. It was revealed that the ruthenium octabutoxyphthalocyanine carbonyl complex [(BuO)8Pc]Ru(CO) is the most efficient catalyst converting electron-rich and electron-poor aromatic olefins to cyclopropane derivatives with high yields (typically 80-100%) and high TON (up to 1000) under low catalyst loading and nearly equimolar substrate/EDA ratio. This catalyst shows a rare efficiency in the carbene insertion into amine N-H bonds. Using a 0.05 mol% catalyst loading, a high amine concentration (1 M) and 1.1 eq. of EDA, a number of structurally divergent amines were selectively converted to mono-substituted glycine derivatives with up to quantitative yields and turnover numbers reaching 2000. High selectivity, large substrate scope, low catalyst loading and practical reaction conditions place [(BuO)8Pc]Ru(CO) among the most efficient catalysts for the carbene insertion into amines.
C-2/C-3 annulation and C-2 alkylation of indoles with 2- alkoxycyclopropanoate esters
Bajtos, Barbora,Yu, Ming,Zhao, Hongda,Pagenkopf, Brian L.
, p. 9631 - 9634 (2008/03/11)
The annulation reaction between various indoles and 2-alkoxycyclopropanoate esters is reported. Both high efficiency and complete stereochemical control were observed in some cases with this annulation process. A single stereocenter on the cyclopropane controls the diastereoselective formation of up to four new stereocenters. A different reaction course was observed with 3-substituted indole substrates, and an intervening C-3 to C-2-migration process arose that gives synthetically useful C-2 alkylation indole products.
Synthesis of Fused Tetrahydrofuran-γ-lactone Motifs via One-Pot Ring Expansion of Cyclopropane Rings
Kom, Charles,Brady, Thomas,Kim, Sun Hee,Theodorakis, Emmanuel A.
, p. 1951 - 1966 (2007/10/03)
An efficient method for constructing fused tetrahydrofuran-γ-lactone scaffolds, such as 8, is presented. Key to this strategy is an acid-catalyzed ring expansion of cyclopropyl precursor 6 that proceeds in the presence of MeSO3H in acetone and produces th