62596-10-5Relevant academic research and scientific papers
D-Aminoacylase-initiated cascade Aldol condensation/Robinson annulation for synthesis of substituted cyclohex-2-enones from simple aldehydes and acetone
Xiang, Ziwei,Liang, Yiru,Chen, Xiang,Wu, Qi,Lin, Xianfu
, p. 1929 - 1937 (2014/08/05)
As an important building block, developing efficient and green synthesis strategy of cyclohex-2-enones is of great importance. In this present work, a general approach to the mild synthesis of substituted cyclohex-2-enones derivatives starting fro m simple aldehydes and acetone have been achieved via D-aminoacylase-initiated Aldol condensation/Robinson annulation cascade reaction using imidazole as an additive in organic media. The influences of reaction conditions including solvents, enzyme concentration, additives type, molar ratio of enzyme to additive, and substrate scopes were systematically investigated. Furthermore, some experiments were designed to explore the catalytic roles of D-aminoacylase and imidazole in the multistep cascade process, and one possible mechanism was proposed.
Rhodium-catalyzed tandem aldol condensation-Robinson annulation between aldehydes and acetone: Synthesis of 3-methylcyclohexenones
Wang, Fen,Liu, Yuchen,Qi, Zisong,Dai, Wei,Li, Xingwei
supporting information, p. 6399 - 6402 (2014/12/10)
A simple catalytic, redox-neutral access to 3-methylcyclohexenones has been developed via rhodium catalysis in the presence of an amine additive and Ag2CO3. This process utilized simple aldehydes and acetone as substrates and tolerates a variety of functional groups. Disubstituted phenols were isolated in moderate yields when Cu(OAc)2 was employed as an oxidant.
L-Lysine/imidazole-catalyzed multicomponent cascade reaction: Facile synthesis of C5-substituted 3-methylcyclohex-2-enones
Xiang, Ziwei,Liu, Zhiqiang,Liang, Yiru,Wu, Qi,Lin, Xianfu
, p. 997 - 1002 (2013/09/02)
A facile and simple route for the direct preparation of substituted 3-methylcyclohex-2-enone via Aldol-Robinson cascade reaction of aldehydes and acetones catalyzed by the new catalytic system of L-lysine/imidazole in n-heptane with 0.5% water was reporte
A tandem Aldol condensation/dehydration co-catalyzed by acylase and N-heterocyclic compounds in organic media
Chen, Xiang,Liu, Bo-Kai,Kang, Hong,Lin, Xian-Fu
body text, p. 71 - 76 (2011/07/07)
A tandem Aldol condensation/dehydration of aldehydes and ketones could be performed under d-aminoacylase and N-heterocyclic compounds used as co-catalyst in organic media. Some control experiments have been designed to demonstrate that either acylase or N-heterocyclic compounds could not catalyze the tandem reaction. The acylase showed the highest activity in the presence of imidazole and has been used to catalyze the tandem Aldol condensation/dehydration between different aldehydes and ketones. This method has provided a new strategy to perform the tandem Aldol condensation/dehydration and expanded the application of biocatalysts.
Organocatalyst-mediated aldolrobinson cascade reactions: A convenient synthesis of substituted cyclohex-2-enones
Wang, Li,Gong, Qing-Ping,Liu, Xiao-Jun,Li, Yong-Hong,Huang, Ping,Wang, Bi-Qin,Zhao, Ke-Qing
supporting information; experimental part, p. 138 - 139 (2011/04/15)
A convenient organocatalytic process for the chemoselective synthesis of substituted cyclohex-2-enones was developed. The cascade reaction involves a remarkable Michael addition of an acyclic ketone-based enamine onto unmodified enones. The enamine-mediated aldolRobinson cascade reactions of aromatic and aliphatic aldehydes with acetone produced substituted cyclohex-2-enones in moderate to high yields under mild reaction conditions.
