Lipase-catalyzed highly diastereoselective direct vinylogous Michael addition reaction of α,α-dicyanoolefins to nitroalkenes

Autor:	Yang Zhang, Wei Zhang, Guan-Nan Chen, Na Wang, Sheng-Yong Yang, Qi Yang, Long-Hua Zhou, Xiao-Qi Yu
Rok vydání:	2014
Předmět:	chemistry.chemical_classification Double bond biology Process Chemistry and Technology Bioengineering Immobilized lipase Mucor miehei Biochemistry Catalysis Enzyme chemistry Docking (molecular) biology.protein Michael reaction Organic chemistry Lipase
Zdroj:	Journal of Molecular Catalysis B: Enzymatic. 109:170-177
ISSN:	1381-1177
DOI:	10.1016/j.molcatb.2014.09.001
Popis:	Lipase-catalyzed direct vinylogous Michael addition reactions of electron-deficient vinyl malononitriles to nitroalkenes are reported for the first time. A series of nitroalkenes reacting with vinyl malononitriles generate the corresponding products with moderate to high yields in the presence of Lipozyme® (immobilized lipase from Mucor miehei) with excellent diastereoselectivities in all reactions under optimized conditions. Docking studies were performed to further elucidate the differences between the various enzymes and substrates. Furthermore, we demonstrated the synthetic potential of the multi-functional products by performing reactions that employed the electron-deficient alkylidene double bond.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::2525f19bf71078acf33080f3bccc198e https://doi.org/10.1016/j.molcatb.2014.09.001 Zobrazit plný text záznamu Full Text from ScienceDirect