627106-80-3Relevant articles and documents
Organocatalytic asymmetric domino Knoevenagel/Diels-Alder reactions: A bioorganic approach to the diastereospecific and enantioselective construction of highly substituted spiro [5,5]undecane-1,5,9-triones
Ramachary,Chowdari, Naidu S.,Barbas III, Carlos F.
, p. 4233 - 4237 (2003)
A practical and environmentally friendly organocatalytic process for the synthesis of optically active highly substituted spiro[5,5]undecane-1,5,9-triones was achieved through the reaction of an aldehyde, an enone, and Meldrum's acid in the presence of a catalytic amount of chiral amino acid (see scheme). The Diels-Alder products were obtained as single diastereomers in excellent yields and enantiomeric excesses.
Stereoselective synthesis of spiro[5.5]undecane derivatives via biocatalytic [5+1] double Michael additions
Chen, Xiao-Yang,Liang, Yi-Ru,Xu, Fang-Li,Wu, Qi,Lin, Xian-Fu
, p. 18 - 22 (2013/10/01)
A novel enzymatic, promiscuous protocol of d-aminoacylase (DA)-catalyzed [5+1] double Michael addition was developed herein, for the synthesis of (hetero)spiro[5.5]undecane derivatives in moderate yields. It is notable that almost only the cis isomers were obtained through this biocatalytic methodology in all the cases according to their 1H and 13C NMR spectra. It is the first report on hydrolase-catalyzed double Michael addition in organic solvent.
Highly efficient synthesis of 3,4-dihydro-2(1H)-quinolinone derivatives under microwave heating
Zhu, Xiao-Tong,Li, Qiu-Yun,Jiang, Bo,Tu, Shu-Jiang
experimental part, p. 1615 - 1628 (2012/08/29)
A sequential three-component reaction of aromatic aldehydes with aromatic amine, and Meldrum's acid in EtOH under microwave irradiation has been developed. In this one-pot reaction, a series of 3,4-dihydro-2(1H)-quinolinone derivatives were synthesized with high chemical yields. The present green synthesis shows several advantages including operational simplicity and fast reaction rate, which makes it a useful and attractive process for library generation for drug discovery.
Sodium acetate catalyzed multicomponent cyclization of aromatic aldehydes, acetone and meldrum acid
An, Lin,Yang, Feng,Yao, Rong,Yan, Chaoguo
experimental part, p. 2451 - 2454 (2011/10/03)
The sodium acetate catalyzed three-component reaction of aromatic aldehyde, acetone and Meldrum acid or spirolactone at room temperature gave stereospecific 7,11-cis-diaryl-2,4-dioxaspiro[5,5]undecane-1,5,9-triones in a very efficient manner. The sodium a
A new domino autocatalytic reaction leading to polyfunctionalized spiro[5.5]undecanes and dispiro[4.2.5.2]pentadecanes
Jiang, Bo,Hao, Wen-Juan,Zhang, Jin-Peng,Tu, Shu-Jiang,Shi, Feng
body text, p. 2195 - 2201 (2009/09/04)
A new domino autocatalytic reaction of imines with Meldrum's acid was described. In this reaction, a series of polycyclic spiro[5.5]undecane-1,5,9- trione and dispiro[4.2.5.2]pentadecane-9,13-dione derivatives, with remarkable diastereoselectivity, were s
Towards organo-click chemistry: Development of organocatalytic multicomponent reactions through combinations of aldol, Wittig, Knoevenagel, Michael, Diels-Alder and Huisgen cycloaddition reactions
Ramachary, Dhevalapally B.,Barbas III, Carlos F.
, p. 5323 - 5331 (2007/10/03)
Here we report on our studies on combinations of amino acids and copper(I) for catalyzing multicomponent reactions (MCRs). We aimed to prepare both diene and dienophiles simultaneously, under very mild and environmentally friendly conditions, thus giving the constituents for a stereocontrolled Diels-Alder reaction, which in turn yields compounds 4 to 8. A diversity-oriented synthesis of polysubstituted spirotriones 4 to 6 were assembled from simple substrates like 1-(triphenylphosphanylidene)-propan-2-one, two aldehydes, and cyclic-1,3-diketones through Wittig/Knoevenagel/Diels-Alder and aldol/Knoevenagel/Diels-Alder reaction sequences in one pot under stereospecific organocatalysis. Chemical diversity libraries of polysubstituted spirotrione-1,2,3-traizoles 8 were assembled from simple substrates by means of Wittig/Knoevenagel/Diels-Alder/Huisgen cycloaddition reaction sequences in one pot under stereospecific organo/CuI catalysis. Functionalized dispirolactones such as 6 are biologically active antioxidants and radical scavengers, and spirotrione-1,2,3-traizoles 8 have found wide applications in chemistry, biology, and materials science. Experimentally simple and environmentally friendly, organocatalytic, asymmetric four-component Diels-Alder (AFCDA) reactions of 1-(triphenylphosphanylidene)-propan-2-one, two different aldehydes, and cyclic-1,3-diketones produced diastereospecific and highly enantioselective substituted spirotriones 4 by means of a Wittig/Knoevenagel/ Diels-Alder reaction sequence in one pot. Additionally we have developed an organocatalytic, asymmetric three-component Michael (ATCM) reaction of 1-(triphenylphosphanylidene)-propan-2-one, aldehyde, and cyclic-1,3-diketones that produced Michael adducts 15, 16 through a Wittig/Michael reaction sequence in a highly enantioselective one-pot process.
