67861-09-0Relevant articles and documents
A novel mesoporous silica-grafted organocatalyst for the Michael addition reaction, synthesized via the click method
Jain, Suman L.,Modak, Arindam,Bhaumik, Asim
, p. 586 - 590 (2011)
An efficient and recyclable mesoporous silica-grafted bifunctional acid-base organocatalyst for the Michael addition of ketones to β-nitrostyrenes has been synthesized by click chemistry, affording the products with excellent diastereoselectivity. A remar
Acidic proteinase from Aspergillus usamii catalyzed Michael addition of ketones to nitroolefins
Xu, Ke-Ling,Guan, Zhi,He, Yan-Hong
body text, p. 108 - 112 (2012/01/13)
A new promiscuous activity of AUAP (acidic proteinase from Aspergillus usamii) was investigated in Michael addition of cyclic and acyclic ketones to aromatic and heteroaromatic nitroolefins in organic media in the presence of water. The yields were obtain
Cyclic nitronates from the diastereoselective addition of 1-trimethylsilyloxycyclohexene to nitroolefins. Starting materials for stereoselective Henry reactions and 1,3-dipolar cycloadditions
Brook, Michael A.,Seebach, Dieter
, p. 836 - 850 (2007/10/02)
Induced by a stoichiometric excess of dichloro(diisopropoxy)-titanium, 1-trimethylsilyloxycyclohexene and (E)-nitroolefins (R-CH=CHNO2, R = C6H5, p-C6H4CH3, p-C6H4OCH3, p-C6H4CN, CH3) combine in CH2Cl2 solution at -90 deg C preferentially with relative topicity ul, opposite to the corresponding reaction of enolates or enamines.The primary products are the epimeric bicyclic nitronates 4-6, which can be separated, and which are converted by KF in MeOH to the alkyl or aryl (nitroethyl)-substituted cyclohexanones 1 and 2 (Table 1).Instead of being solvolysed, the cyclic nitronates 4-6 can be used for nitroaldol additions to give the trisubstituted hexahydrobenzopyranols 15-19.Alternatively, 4-6 can be used in 1,3-dipolar cycloadditions with acrylates to furnish the tricyclic compounds 22-31.In either case, products with four asymmetric carbon atoms (not including acetal centres) are produced diastereoselectively.The addition described here is yet another example of an ul combination of trigonal centres induced by Lewis acids, overriding the influence of the configuration of the donor component.