Citation: You-Qing Wang, Yuan-Yuan Ren. Highly enantioselective direct Mannich reaction of seven-membered cyclic imines dibenzo[b,f][1,4]oxazepines with acetone via organocatalysis[J]. Chinese Journal of Catalysis, ;2015, 36(1): 93-99. doi: 10.1016/S1872-2067(14)60225-4 shu

Highly enantioselective direct Mannich reaction of seven-membered cyclic imines dibenzo[b,f][1,4]oxazepines with acetone via organocatalysis

You-Qing Wang ^, ,
Yuan-Yuan Ren

1.
Provincial Key Laboratory of Natural Medicine and Immuno-Engineering, Henan University, Kaifeng 475004, Henan, China

Corresponding author: You-Qing Wang,
Received Date: 14 August 2014
Available Online: 12 September 2014
Fund Project: 国家自然科学基金(21002022) (21002022)

Various substituted dibenzo[b,f][1,4]oxazepines as seven-membered cyclic imines underwent a highly enantioselective direct Mannich reaction with acetone when catalyzed by proline. These reactions gave a range of optically active β-carbonyl seven-membered N-heterocycles with excellent enantioselectivity (93%-98% ee). With 2-butanone as a Mannich donor, the single regioselective product was obtained with 96%-97% ee. The absolute configuration of the product was assigned to be R by X-ray single crystal analysis of its derivative.
- Acetone,
- Asymmetric catalysis,
- Seven-membered cyclic imine,
- Mannich reaction,
- Organocatalysis
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