An Efficient Ionic Liquid Additive for Proline-catalyzed Direct Asymmetric Aldol Reactions between Cyclic Ketones and Aromatic Aldehydes

2009 ◽  
Vol 38 (6) ◽  
pp. 576-577 ◽  
Author(s):  
Yunbo Qian ◽  
Xin Zheng ◽  
Xu Wang ◽  
Shiyong Xiao ◽  
Yongmei Wang
Keyword(s):  
Ionic Liquid ◽  
Aromatic Aldehydes ◽  
Aldol Reactions ◽  
Cyclic Ketones ◽  
Asymmetric Aldol

L-Proline in an Ionic Liquid as an Efficient and Reusable Catalyst for Direct Asymmetric Aldol Reactions.

ChemInform ◽  
2003 ◽  
Vol 34 (7) ◽  
Author(s):  
Teck-Peng Loh ◽  
Li-Chun Feng ◽  
Hai-Yan Yang ◽  
Jian-Ying Yang
Keyword(s):  
Ionic Liquid ◽  
Aldol Reactions ◽  
Reusable Catalyst ◽  
Asymmetric Aldol

scholarly journals Novel chiral ionic liquid (CIL) assisted selectivity enhancement to (L)-proline catalyzed asymmetric aldol reactions

2011 ◽  
Vol 22 (9) ◽  
pp. 1736-1741 ◽  
Author(s):  
Long Zhang ◽  
Haibo Zhang ◽  
Huadong Luo ◽  
Xiaohai Zhou ◽  
Gongzhen Cheng
Keyword(s):  
Ionic Liquid ◽  
Aldol Reactions ◽  
Asymmetric Aldol ◽  
Chiral Ionic Liquid

Asymmetric aldol reactions in ketone/ketone systems catalyzed by ionic liquid-supported C2-symmetrical organocatalyst

2015 ◽  
Vol 25 (3) ◽  
pp. 168-170 ◽  
Author(s):  
Sergei V. Kochetkov ◽  
Alexander S. Kucherenko ◽  
Sergei G. Zlotin
Keyword(s):  
Ionic Liquid ◽  
Aldol Reactions ◽  
Asymmetric Aldol

Direct Asymmetric Aldol Reactions Catalyzed by Lipase from Porcine Pancreas

2014 ◽  
Vol 69 (3-4) ◽  
pp. 170-180 ◽  
Author(s):  
Jing Zheng ◽  
Bang-Hua Xie ◽  
Yan-Li Chen ◽  
Jian-Fei Cao ◽  
Yang Yang ◽  
...  
Keyword(s):  
Organic Synthesis ◽  
Aldol Reactions ◽  
Type Ii ◽  
Cyclic Ketones ◽  
Porcine Pancreas ◽  
Asymmetric Aldol ◽  
Porcine Pancreas Lipase ◽  
Wide Range ◽  
Valuable Method ◽  
High Yields

Porcine pancreas lipase type II (PPL II) exhibited unnatural catalytic activity in direct asymmetric aldol reactions between cyclic ketones and aromatic or heteroaromatic aldehydes in acetonitrile in the presence of phosphate buffer. A wide range of substrates was accepted by the enzyme to afford the corresponding aldol products in low to high yields (10 - 98%), with moderate to excellent enantioselectivities (53 - 94% ee, for anti-isomers) and low to moderate diastereoselectivities (48/52 - 87/13 dr, anti/syn). This methodology expands the application of PPL II, and it might be developed into a potentially valuable method for sustainable organic synthesis.

scholarly journals Chiral Thiazolidine based Organocatalysts: Synthesis and Application in Asymmetric Aldol Reactions

2020 ◽  
Vol 17 (5) ◽  
pp. 372-380
Author(s):  
Ana Rita G. Félix ◽  
Pedro R.D. Simões ◽  
Francisco J.P.M. Sousa ◽  
M. Elisa Silva Serra ◽  
Dina Murtinho
Keyword(s):  
Reaction Time ◽  
Aldol Reaction ◽  
Aromatic Aldehydes ◽  
Aldol Reactions ◽  
Catalyst Loading ◽  
Reaction Parameters ◽  
Asymmetric Aldol ◽  
Asymmetric Aldol Reaction

Several novel chiral organocatalysts derived from thiazolidines containing amide and thioureia functionalities were synthesized in good yields. These organocatalysts were tested in the asymmetric aldol reaction of acetone with p-nitrobenzaldehyde. Reaction parameters such as reaction time, catalyst loading and solvent were optimized. Products with conversions up to 84% and enantiomeric ratios (er) up to 84.5:15.5 (R:S) were obtained. The effect of several chiral and non-chiral additives on the reactivity and selectivity of the reaction was also evaluated. The reaction was extended to other aromatic aldehydes with the best organocatalyst and when p-bromobenzaldehyde was used, an er of 94.5:5.5 (R:S) was obtained.

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