78548-58-0Relevant academic research and scientific papers
A diastereoselective synthesis of boceprevir's gem-dimethyl bicyclic [3.1.0] proline intermediate from an insecticide ingredient cis-cypermethric acid
Kallam, Srinivasa Reddy,Eda, Vishnuvardhan Reddy,Sen, Saikat,Datrika, Rajender,Rapolu, Rajesh Kumar,Khobare, Sandip,Gajare, Vikas,Banda, Malavika,Khan, Rashid Abdul Rehman,Singh, Manpreet,Lloyd, Michael,Kandagatla, Bhaskar,Janagili, Moses Babu,Tadikonda, Veerabhadra Pratap,Vidavalur, Siddaiah,Iqbal, Javed,Fox, Martin E.,Dahanukar, Vilas H.,Oruganti, Srinivas
, p. 4285 - 4294 (2017)
An efficient multi-gram synthesis of (1R,2S,5S)-methyl 6,6-dimethyl-3-azabicyclo[3.1.0]hexane-2-carboxylate, a key chiral bicyclic proline fragment employed in the construction of the potent anti-HCV drug boceprevir, has been presented. The synthetic route commences with the readily available cis-cypermethric acid, a cheap source of the cyclopropane ring required in the targeted compound, and utilizes the cis-orientation of the 2,2-dichlorovinyl and carboxylic acid side arms, already present in the starting material, to effect a diastereoselective construction of the proline moiety.
Cyclopropanation of olefins by ethyl diazoacetate: copper- and copper-complex-containing X-zeolites as the catalysts
Oudejans, J.C.,Kaminska, J.,Dalen, A. C. Kock-van,Bekkum, H. van
, p. 421 - 427 (2007/10/02)
Cyclopropanation of olefins by ethyl diazoacetate has been carried out making use of the catalytic action of Cu-loaded X-type zeolites upon the decomposition of ethyl diazoacetate.The activity of the NaCuX zeolites is linearly dependent upon the Na-exchange level.Compared to conventional copper catalysts, the zeolite catalysts give rise to relatively low amounts of polymeric side-product which is assumed to be formed at the outer zeolite surface.The stereoselectivity obtained with the zeolite catalysts does not deviate significantly from that obtained using copper salts.Zeolite X, loaded with chiral copper complexes, gives rise to only minor asymmetric induction upon cyclopropanation of 1,1-dichloro-4-methyl-1,3-pentadiene with ethyl diazoacetate.
