D-Aminoacylase-initiated cascade Aldol condensation/Robinson annulation for synthesis of substituted cyclohex-2-enones from simple aldehydes and acetone.
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.
Department of Chemistry, Zhejiang University, 310027, Hangzhou, People's Republic of China.
Ziwei
Z
Xiang
Yiru
Y
Liang
Xiang
X
Chen
Qi
Q
Wu
Xianfu
X
Lin
D000096:Acetone / Q000737:chemistry / Q000378:metabolism; D000447:Aldehydes / Q000737:chemistry / Q000378:metabolism; D000581:Amidohydrolases / Q000737:chemistry / Q000378:metabolism*; D002384:Catalysis; D003500:Cyclization; D003511:Cyclohexanols / Q000138:chemical synthesis*; D007093:Imidazoles / Q000737:chemistry; D015394:Molecular Structure
D000447:Aldehydes; D003511:Cyclohexanols; D007093:Imidazoles; D000096:Acetone; C116609:3-hydroxybutanal; D000581:Amidohydrolases; C019672:aminoacylase I