An environmentally benign double Michael addition reaction of heterocyclic ketene aminals with quinone monoketals for diastereoselective synthesis of highly functionalized morphan derivatives in water

作者：Ma, Yu-Lu; Wang, Kai-Min; Huang, Rong; Lin, Jun^*; Yan, Sheng-Jiao^*

来源：Green Chemistry, 2017, 19(15): 3574-3584.

DOI：10.1039/c7gc01435j

• DIELS-ALDER CYCLOADDITIONS
• OPIOID DELTA-RECEPTOR
• ONE-POT SYNTHESIS
• CASCADE REACTION
• REGIOSELECTIVE SYNTHESIS
• SPIROOXINDOLE DERIVATIVES
• ANTAGONIST
• ROUTE
• CONSTRUCTION
• MONOACETALS

A efficient and concise one-pot procedure has been developed for the synthesis of highly functional morphan derivatives 3 based on diastereoselective double Michael addition reactions of various quinone monoketals 1 with a variety of heterocyclic ketene aminals (HKAs) 2 in the green solvent water at 60 degrees C. This protocol is especially suitable for efficient and rapid parallel syntheses of N-containing bridged heterocycles possessing pharmacological activities. As a result, a library of highly functional morphan derivatives was easily synthesized using this reported environmentally benign, mild, and catalyst-free one-pot reaction.

• 出版日期2017-8-7
• 单位云南大学