scholarly journals Asymmetric Michael Addition of Malononitrile with Chalcones via Rosin-Derived Bifunctional Squaramide

Catalysts ◽  
2019 ◽  
Vol 10 (1) ◽  
pp. 14
Author(s):  
Ning Lin ◽  
Qiu-Xiang Wei ◽  
Li-Hua Jiang ◽  
Yan-Qiu Deng ◽  
Zhen-Wei Zhang ◽  
...  
Keyword(s):  
Michael Addition ◽  
Carbonyl Compounds ◽  
Catalyst Loading ◽  
Facile Synthesis ◽  
Asymmetric Michael Addition ◽  
High Yields ◽  
Experimental Findings

A rosin-derived bifunctional squaramide catalyzed asymmetric Michael addition of malononitrile with chalcones was discovered. This protocol provides a methodology for the facile synthesis of chiral γ-cyano carbonyl compounds in high yields and enantioselectivities (up to 99% yield and 90% ee) with a lower catalyst loading (0.3 mol%). The predominant R-configured adducts were obtained by this organocatalystic reaction, according to the experimental findings.

Highly Enantioselective Michael Addition of Cyclic Diketones to β,γ-Unsaturated α-Keto Esters Catalyzed by Squaramide Organocatalyst

Synthesis ◽  
2022 ◽  
Author(s):  
Zhi-Wei Ma ◽  
Chuan-Chuan Wang ◽  
Quan-Jian Lv ◽  
Xiao-Pei Chen ◽  
Ai-Qin Li ◽  
...  
Keyword(s):  
Michael Addition ◽  
Large Scale ◽  
Catalyst System ◽  
Catalyst Loading ◽  
Reaction Conditions ◽  
Keto Esters ◽  
Bicyclic Compounds ◽  
Asymmetric Michael Addition ◽  
High Yields ◽  
Low Catalyst Loading

AbstractA new tertiary amine-squaramide organocatalyst has been developed and applied to the asymmetric Michael addition of cyclic diketones to β,γ-unsaturated α-keto esters. The catalyst system performed well with a low catalyst loading of 1 mol% under mild reaction conditions. A series of synthetically and pharmaceutically useful chiral bicyclic compounds were obtained in high yields (up to 97%) with excellent enantioselectivities (up to 99 % ee). Furthermore, this catalytic system can be used efficiently in large-scale reactions with the yields and enantioselectivities being maintained.

Facile Synthesis of 2-Arylindoles through Plancher-Type Rearrangement of 3-Alkyl-3-Arylindolenines

Synlett ◽  
2017 ◽  
Vol 28 (15) ◽  
pp. 1994-1999
Author(s):  
Santhosh Chittimalla ◽  
Chennakesavulu Bandi ◽  
Vinod Gadi ◽  
Siva Gunturu
Keyword(s):  
Michael Addition ◽  
Facile Synthesis ◽  
Type C ◽  
High Yields

3-Alkylindoles on reaction with a cyclohexa-2,4-dien-1-one catalyzed by BF3·OEt2 gave the corresponding 3-alkyl-3-arylindolenines in high yields through a tandem Michael addition/aromatization sequence. In the presence of HCl, these indolenine derivatives underwent a facile Plancher-type C-3 to C-2 aryl rearrangement to deliver the corresponding 2-arylindoles.

scholarly journals Michael addition of carbonyl compounds to nitroolefins under the catalysis of new pyrrolidine-based bifunctional organocatalysts

2018 ◽  
Vol 16 (6) ◽  
pp. 924-935 ◽  
Author(s):  
A. Castán ◽  
R. Badorrey ◽  
J. A. Gálvez ◽  
P. López-Ram-de-Víu ◽  
M. D. Díaz-de-Villegas
Keyword(s):  
Michael Addition ◽  
Carbonyl Compounds ◽  
Asymmetric Michael Addition ◽  
Aldehydes And Ketones

Novel bifunctional pyrrolidine-based organocatalysts applicable for the asymmetric Michael addition of aldehydes and ketones to nitroolefins have been developed.

scholarly journals Enantioselective Michael addition of 2-hydroxy-1,4-naphthoquinones to nitroalkenes catalyzed by binaphthyl-derived organocatalysts

2012 ◽  
Vol 8 ◽  
pp. 699-704 ◽  
Author(s):  
Saet Byeol Woo ◽  
Dae Young Kim
Keyword(s):  
Michael Addition ◽  
Catalyst Loading ◽  
High Yields ◽  
Low Catalyst Loading

The highly enantioselective Michael addition of 2-hydroxy-1,4-naphthoquinones to nitroalkenes, promoted by binaphthyl-modified chiral bifunctional organocatalysts is described. This reaction afforded the chiral functionalized naphthoquinones in high yields (81–95%) and excellent enantioselectivities (91–98% ee) under low catalyst loading (1 mol %).

Highly Enantioselective Michael Addition of Dithiomalonates to Nitroolefins Catalyzed by New Bifunctional Chiral Thioureas

Synthesis ◽  
2018 ◽  
Vol 50 (13) ◽  
pp. 2577-2586 ◽  
Author(s):  
Jia-Ni Yuan ◽  
Hui-Xia Liu ◽  
Qin-Qin Tian ◽  
Nan Ji ◽  
Kuo Shen ◽  
...  
Keyword(s):  
Michael Addition ◽  
Mild Conditions ◽  
Highly Efficient ◽  
Michael Adducts ◽  
Asymmetric Michael Addition ◽  
High Yields

We report a highly efficient asymmetric Michael addition of dithiomalonates to trans-β-nitroolefins catalyzed by versatile cinchona-based bifunctional thioureas, which provides the corresponding adducts in high yields (up to 92%) and with excellent enantioselectivities (up to 99% ee) under mild conditions. Replacement of the catalyst with its pseudo-enantiomer gives the Michael adducts with opposite configuration in similar yields and enantioselectivities.

A solution to achieve good reusability of MNPs Fe3O4-supported (S)-diphenylprolinoltrimethylsilyl ether catalysts in asymmetric Michael reactions

RSC Advances ◽  
2016 ◽  
Vol 6 (30) ◽  
pp. 25246-25254 ◽  
Author(s):  
Tao Wu ◽  
Dandan Feng ◽  
Bing Xie ◽  
Xuebing Ma
Keyword(s):  
Michael Addition ◽  
Michael Reactions ◽  
Asymmetric Michael Addition ◽  
High Yields

A PVP-modified MNPs Fe3O4-supported Jøgensen–Hayashi catalyst to achieved good reusability with high yields and unchangeable excellent stereoselectivities in the asymmetric Michael addition of propanal to nitroalkenes.

Potassium Hydroxide Catalysed Intermolecular Aza-Michael Addition of 3-Cyanoindole to Aromatic Enones

Synlett ◽  
2017 ◽  
Vol 28 (10) ◽  
pp. 1227-1231 ◽  
Author(s):  
Jingya Yang ◽  
Tianyuan Li ◽  
Hongyan Zhou ◽  
Nana Li ◽  
Dongtai Xie ◽  
...  
Keyword(s):  
Reaction Temperature ◽  
Michael Addition ◽  
Potassium Hydroxide ◽  
Michael Reaction ◽  
Pharmaceutical Compounds ◽  
Catalyst Loading ◽  
Good Substrate ◽  
Substrate Tolerance ◽  
High Yields ◽  
Low Catalyst Loading

Indole is one of the utmost important heterocycles as it is an essential nucleus of many pharmaceutical compounds. Its aza-Michael reaction, however, is underdeveloped because of the moiety’s inherent characteristics. Here, a potassium hydroxide catalysed intermolecular aza-Michael reaction of 3-cyanoindole with aromatic enones is described. A variety of chalcone derivatives are well tolerated and afford the corresponding N-adducts in moderate to high yields. The use of a cheap catalyst, low catalyst loading, mild reaction temperature, and good substrate tolerance make this procedure a direct and facile method for the preparation of N1-functionalized indoles.

Squaramide-catalysed asymmetric cascade reactions of 2,3-dioxopyrrolidines with 3-chlorooxindoles

2020 ◽  
Vol 18 (8) ◽  
pp. 1647-1656 ◽  
Author(s):  
Jiang-Bo Wen ◽  
Da-Ming Du
Keyword(s):  
Michael Addition ◽  
Cascade Reactions ◽  
Cascade Reaction ◽  
Spiro Compounds ◽  
Asymmetric Michael Addition ◽  
High Yields

An efficient squaramide-catalysed asymmetric Michael addition/cyclization cascade reaction of 3-chlorooxindoles with 2,3-dioxopyrrolidines produced the corresponding chiral spiro-compounds in high yields with excellent stereoselectivities.

Sign in / Sign up

Export Citation Format

Share Document