Asymmetric Morita-Baylis-Hillman Reaction of Conjugated Nitroalkene with Activated Aldehyde Catalyzed by Cinchona Alkaloids / 中国药师
China Pharmacist
;
(12): 216-220, 2017.
Article
in Chinese
| WPRIM
| ID: wpr-507508
ABSTRACT
Objective:
To develop a catalytic system for the asymmetric Morita-Baylis-Hillman ( MBH) reaction of conjugated ni-troalkene with activated aldehyde, and screen out the chiral catalysts with high activity and enantioselectivity.Methods:
Totally 21 chiral organocatalysts were applied in the asymmetric MBH reaction ofβ-nitrostyrene with ethyl glyoxylate, and the ee value was deter-mined by chiral HPLC. The effects of temperature, solvent and substrate ratio on the catalytic reaction were investigated.Results:
In the presence of cinchona alkaloid catalyst (DHQ)2AQN, β-nitrostyrene reacted with ethyl glyoxylate in toluene at 0℃ affording the MBH adduct in 60% yield with good enantioselectivity (up to 56.9% ee).Conclusion:
The bis-cinchona alkaloids with aromatic bridging group are the efficient catalysts for the asymmetric MBH reaction ofβ-nitrostyrene with ethyl glyoxylate, and moderate isolated yield and enantioselectivity are obtained.
Full text:
Available
Index:
WPRIM (Western Pacific)
Language:
Chinese
Journal:
China Pharmacist
Year:
2017
Type:
Article
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