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.

Squaramide−catalysed asymmetric Michael addition/cyclization cascade reactions of 4-arylidene-2,3-dioxopyrrolidines with 2-isothiocyanato-1-indanones

2021 ◽  
Author(s):  
Xiqiang Hou ◽  
Jiang-Bo Wen ◽  
Li Yan ◽  
Da-Ming Du
Keyword(s):  
Michael Addition ◽  
Cascade Reactions ◽  
Cascade Reaction ◽  
Cinchona Alkaloid ◽  
Highly Efficient ◽  
Asymmetric Michael Addition

A highly efficient cinchona alkaloid‐derived squaramide catalysed asymmetric Michael/cyclization cascade reaction of 4‐ arylmethylidene‐2,3‐dioxopyrrolidines with 2‐isothiocyanato‐1‐indanones was successfully developed. This protocol provides an efficient and mild access to obtain indanone‐derived...

scholarly journals Synthesis of indanes via carbene-catalyzed single-electron-transfer processes and cascade reactions

2017 ◽  
Vol 53 (87) ◽  
pp. 11952-11955 ◽  
Author(s):  
Yuhuang Wang ◽  
Xingxing Wu ◽  
Yonggui Robin Chi
Keyword(s):  
Electron Transfer ◽  
Michael Addition ◽  
Cascade Reactions ◽  
Cascade Reaction ◽  
Single Electron ◽  
Single Electron Transfer ◽  
Transfer Processes ◽  
Electron Transfer Processes

An NHC-catalyzed cascade reaction involving an SET process and two sequential Michael addition steps for the synthesis of indanes is disclosed.

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.

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.

Fe-Catalyzed Bisphosphorylation of Amino-2-en-1-ones with Trialkyl Phosphites

Synlett ◽  
2019 ◽  
Vol 30 (09) ◽  
pp. 1090-1094 ◽  
Author(s):  
Shengmei Guo ◽  
Kun Jie ◽  
Ling Huang ◽  
Zhebin Zhang ◽  
Yufeng Wang ◽  
...  
Keyword(s):  
Michael Addition ◽  
Functional Group ◽  
Cascade Reaction ◽  
Trialkyl Phosphites ◽  
High Yields

A facile bisphosphorylation of amino-2-en-1-ones with trialkyl phosphites mediated by iron is developed. The reaction is considered to go through two Michael addition progresses. A variety of amino-2-en-1-ones are bisphosphorylated in high yields with functional group tolerance. In addition, the protocol of introduction of two different phosphates into one molecule is successful through a cascade reaction.

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.

Reaction of Bromoenones with Amidines: A Simple Catalyst-Free Approach to Trifluoromethylated Pyrimidines

Synthesis ◽  
2020 ◽  
Vol 52 (10) ◽  
pp. 1512-1522
Author(s):  
Alexander Yu. Rulev ◽  
Alexey R. Romanov ◽  
Alexander V. Popov ◽  
Evgeniy V. Kondrashov ◽  
Sergey V. Zinchenko
Keyword(s):  
Intramolecular Cyclization ◽  
Michael Addition ◽  
High Selectivity ◽  
Reaction Path ◽  
Cascade Reactions ◽  
Trifluoromethyl Group ◽  
Reaction Conditions ◽  
One Pot ◽  
One Pot Synthesis ◽  
High Yields

A facile one-pot synthesis of trifluoromethylated pyrimidines has been achieved by the treatment of fluorinated 2-bromoenones with aryl- and alkylamidines. The assembly of pyrimidine core proceeds by the cascade reactions via aza-Michael addition–intramolecular cyclization–dehydrohalogenation/dehydration sequence. This strategy is featured by high selectivity and mild reaction conditions giving the target heterocycles in high yields (up to 99%). The unique influence of trifluoromethyl group on the reaction path is demonstrated.

Asymmetric organocatalytic vinylogous Michael addition triggered triple-cascade reactions of 2-hydroxycinnamaldehydes and vinylogous nucleophiles: Construction of Benzofused Oxabicyclo[3.3.1]nonane Scaffolds

2021 ◽  
Author(s):  
Hui-Chun Wu ◽  
Chen Wang ◽  
Ying-Han Chen ◽  
Yankai Liu
Keyword(s):  
Michael Addition ◽  
Cascade Reactions ◽  
Cascade Reaction ◽  
Cyclic Ketone

An organocatalytic vinylogous Michael addition triggered triple-cascade reaction has been developed. 2-Hydroxycinnamaldehydes worked under iminium activation with either acyclic or cyclic ketone-derived α,α-dicyanoalkenes, yielding the benzofused oxabicyclo[3.3.1]nonanes bearing one quaternary...

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