132895-22-8Relevant academic research and scientific papers
Enantioselective Redox-Divergent Chiral Phosphoric Acid Catalyzed Quinone Diels–Alder Reactions
Bernadat, Guillaume,Gelis, Coralie,Masson, Géraldine,Neuville, Luc,Retailleau, Pascal,Varlet, Thomas
, p. 8491 - 8496 (2020)
An efficient enantioselective construction of tetrahydronaphthalene-1,4-diones as well as dihydronaphthalene-1,4-diols by a chiral phosphoric acid catalyzed quinone Diels–Alder reaction with dienecarbamates is reported. The nature of the protecting group on the diene is key to the success of achieving high enantioselectivity. The divergent “redox” selectivity is controlled by using an adequate amount of quinones. Reversible redox switching without erosion of enantioselectivity was possible from individual redox isomers.
Double reformatsky reaction: Divergent synthesis of δ-hydroxy-β- ketoesters
Mineno, Masahiro,Sawai, Yasuhiro,Kanno, Kazuaki,Sawada, Naotaka,Mizufune, Hideya
, p. 5843 - 5850 (2013/07/26)
The double Reformatsky reaction, tandem addition of two molecules of zinc alkanoate to a carbonyl compound, and its synthetic application to a series of δ-hydroxy-β-ketoesters has been developed. The key to accelerate the double Reformatsky reaction is considered to be a complex-induced proximity effect of the in situ generated zinc alkoxide coordinated with the pyridyl group of the substrate or bidentate amines. A noteworthy feature of the reaction system is its high tolerance of functional groups due to the moderate nucleophilicity of organozinc reagents and the mild reaction conditions. Moreover, spectroscopic and crystallographic analyses of the zinc complex of the double Reformatsky product support the proposed mechanism of reaction site discrimination for ketones, aldehydes, nitriles, carboxylic acid anhydrides, and esters.
Concise stereoselective total synthesis of (4 R, 6 R)-lactone moiety analog of mevinoline and compactin
Rao, D. Chandra,Reddy, D. Kumar,Chinnababu,Shekhar,Venkateswarlu
, p. 2980 - 2984 (2013/09/12)
A simple and highly efficient synthetic route has been developed for analogue of HMGCo A reductase inhibitor (1). The strategy utilizes S-Corey-Bakshi-Shibata (CBS) reduction, FeCl3-catalyzed C-H insertion of ethyl diazoacetate.
Stereoselective synthesis of a mevinic acid analogue
Sabitha, Gowravaram,Sudhakar,Srinivas,Yadav
, p. 705 - 708 (2007/12/29)
An efficient and versatile synthetic method for the stereoselective synthesis of a mevinic acid analogue is described. This approach uses a combination of a Cosford protocol with a catecholborane-mediated stereoselective reduction of acyclic P-hydroxy ket
