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.

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

Highly modular dipeptide-like organocatalysts for direct asymmetric aldol reactions in brine

RSC Advances ◽  
2015 ◽  
Vol 5 (49) ◽  
pp. 39557-39564 ◽  
Author(s):  
Xiao-Mu Hu ◽  
Dong-Xu Zhang ◽  
Sheng-Yong Zhang ◽  
Ping-An Wang
Keyword(s):  
Aldol Reactions ◽  
Catalyst Loading ◽  
Asymmetric Aldol ◽  
High Yields

The dipeptide-like organocatalysts have been developed for asymmetric aldol reactions in brine to achieve high yields and enantioselectivities with 1 mol% catalyst-loading.

scholarly journals Earthworms as a Biocatalyst: In Asymmetric Aldol Reactions

2017 ◽  
Vol 22 (9) ◽  
pp. 1162-1167
Author(s):  
Guo-Yan Zhang ◽  
Yan-Li Chen ◽  
Hai-Hong Li ◽  
Zhi Guan ◽  
Yan-Hong He
Keyword(s):  
Crude Extract ◽  
Industrial Production ◽  
Carbonyl Compounds ◽  
Large Scale ◽  
Environmentally Friendly ◽  
Aldol Reactions ◽  
Asymmetric Aldol ◽  
Excellent Yield ◽  
Wide Range ◽  
Potential Possibility

A crude extract from earthworms was used as an environmentally friendly and easily accessible biocatalyst for asymmetric direct aldol reactions. The β-hydroxy carbonyl compounds could be prepared in yields of up to 94%, with ee values of up to 98% and dr of up to >99:1. A wide range of substrates could participate in the reaction. This earthworm catalyst was also efficient in the large-scale reaction, providing product in excellent yield and good selectivity. The protocol as an example gives inspiration for the development of sustainable catalysts from nature, which also provides a potential possibility for application of earthworm catalyst in industrial production.

Catalytic asymmetric aldol addition reactions of 3-fluoro-indolinone derived enolates

2017 ◽  
Vol 15 (2) ◽  
pp. 311-315 ◽  
Author(s):  
Lijun Zhang ◽  
Wenzhong Zhang ◽  
Haibo Mei ◽  
Jianlin Han ◽  
Vadim A. Soloshonok ◽  
...  
Keyword(s):  
Aldol Reactions ◽  
Addition Reactions ◽  
Asymmetric Aldol ◽  
Wide Range ◽  
Stereogenic Centers ◽  
New Type ◽  
Catalytic Asymmetric ◽  
Aldol Addition ◽  
Quaternary Stereogenic Centers

Cu(i)/bisoxazoline ligand catalyzed asymmetric aldol reactions of fluoro-indolinone derived new type tertiary enolates have been developed. This process allows the preparation of a wide range of α-fluoro-β-aryl/hetaryl/alkyl-β-hydroxy-indolin-2-one products containing C–F quaternary stereogenic centers.

Organoboron compounds in organic synthesis. 4. Asymmetric aldol reactions

1986 ◽  
Vol 108 (26) ◽  
pp. 8279-8281 ◽  
Author(s):  
Satoru. Masamune ◽  
Tsuneo. Sato ◽  
ByeongMoon. Kim ◽  
Theodor A. Wollmann
Keyword(s):  
Organic Synthesis ◽  
Aldol Reactions ◽  
Asymmetric Aldol ◽  
Organoboron Compounds

scholarly journals Palladium-catalyzed regio- and enantioselective migratory allylic C(sp3)-H functionalization

2021 ◽  
Vol 12 (1) ◽  
Author(s):  
Ye-Wei Chen ◽  
Yang Liu ◽  
Han-Yu Lu ◽  
Guo-Qiang Lin ◽  
Zhi-Tao He
Keyword(s):  
Organic Synthesis ◽  
Allylic Substitution ◽  
Palladium Hydride ◽  
Substitution Process ◽  
Wide Range ◽  
Leaving Group ◽  
Palladium Catalyzed ◽  
Potential Factors ◽  
Metal Catalyzed ◽  
High Yields

AbstractTransition metal-catalyzed asymmetric allylic substitution with a suitably pre-stored leaving group in the substrate is widely used in organic synthesis. In contrast, the enantioselective allylic C(sp3)-H functionalization is more straightforward but far less explored. Here we report a catalytic protocol for the long-standing challenging enantioselective allylic C(sp3)-H functionalization. Through palladium hydride-catalyzed chain-walking and allylic substitution, allylic C-H functionalization of a wide range of acyclic nonconjugated dienes is achieved in high yields (up to 93% yield), high enantioselectivities (up to 98:2 er), and with 100% atom efficiency. Exploring the reactivity of substrates with varying pKa values uncovers a reasonable scope of nucleophiles and potential factors controlling the reaction. A set of efficient downstream transformations to enantiopure skeletons showcase the practical value of the methodology. Mechanistic experiments corroborate the PdH-catalyzed asymmetric migratory allylic substitution process.

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