5300-06-1Relevant academic research and scientific papers
Regioselective Monoalkylation of Ketones with Allylic Nitro Compounds
Ono, Noboru,Hamamoto, Isami,Kaji, Aritsune
, p. 1863 - 1864 (1985)
Lithium enolates from 2-methylcyclohexanone and p-methylacetophenone react with allylic nitro compounds in the presence of triethylborane (2 equiv) and Pd(PPh3)4 (5 molpercent) to give monoallylated compounds regioselectively.
Radical Aza-Cyclization of α-Imino-oxy Acids for Synthesis of Alkene-Containing N-Heterocycles via Dual Cobaloxime and Photoredox Catalysis
Tu, Jia-Lin,Liu, Jia-Li,Tang, Wan,Su, Ma,Liu, Feng
, p. 1222 - 1226 (2020/02/15)
Nitrogen-containing heterocycles are prevalent in both naturally and synthetically bioactive molecules. We report herein an unprecedented protocol for radical aza-cyclization of α-imino-oxy acids with pendant alkenes via synergistic photoredox and cobaloxime catalysis. With or without alkenes as the intermolecular cross-coupling partners, the transformation provides a variety of corresponding alkene-containing dihydropyrrole products in satisfactory yields. In the presence of external alkenes, the tandem reaction generates E-selective coupling products with excellent chemo- and stereoselectivity.
Very short highly enantioselective Grignard synthesis of 2,2-disubstituted tetrahydrofurans and tetrahydropyrans
Monasterolo, Claudio,Müller-Bunz, Helge,Gilheany, Declan G.
, p. 6531 - 6538 (2019/07/10)
Phenones with elongated chains are shown to be excellent substrates for ligand-promoted asymmetric Grignard synthesis of tertiary alcohols. In turn this enables the simple, short and highly enantioselective (up to 96% ee) preparation of chiral 2,2-disubst
Cyclization-endoperoxidation cascade reactions of dienes mediated by a pyrylium photoredox catalyst
Gesmundo, Nathan J.,Nicewicz, David A.
supporting information, p. 1272 - 1281 (2014/06/24)
Triarylpyrylium salts were employed as single electron photooxidants to catalyze a cyclization-endoperoxidation cascade of dienes. The transformation is presumed to proceed via the intermediacy of diene cation radicals. The nature of the diene component was investigated in this context to determine the structural requirements necessary for successful reactivity. Several unique endoperoxide structures were synthesized in yields up to 79%.
Enantioselective synthesis of (+)-gossonorol and related systems using organozinc reagents
Gonzalez-Lopez, Susana,Yus, Miguel,Ramon, Diego J.
, p. 611 - 615 (2012/08/13)
The sesquiterpene (+)-gossonorol is prepared in only three synthetic steps in 60% overall yield and 82% ee from commercially available reagents. The key asymmetric step is the catalytic enantioselective addition of dimethylzinc to 5-methyl-1-(2-methylphen
Synthesis of biaryls via AlCl3 catalyzed domino reaction involving cyclization, dehydration, and oxidation
Narender, Tadigoppula,Sarkar, Satinath,Rajendar, Kandikonda,Tiwari, Sriniwas
supporting information; experimental part, p. 6140 - 6143 (2012/01/03)
A new chemical access has been developed to synthesize biaryls from substituted acetophenones, phenylacetones, dihydrochalcone, and 2-acetylnaphthalene in reasonably good yields at room temperature via a domino reaction sequence of AlCl3 catalyzed cyclization, dehydration, and then oxidation.
