Asymmetric Organocatalytic Michael Addition–Cyclization Cascade of Cyclopentane-1,2-dione with Substituted α,β-Unsaturated Aldehydes

Synthesis ◽  
2017 ◽  
Vol 49 (14) ◽  
pp. 3118-3125 ◽  
Author(s):  
Margus Lopp ◽  
Gert Preegel ◽  
Estelle Silm ◽  
Sandra Kaabel ◽  
Ivar Järving ◽  
...  
Keyword(s):  
Michael Addition ◽  
Cascade Reaction ◽  
One Pot ◽  
Unsaturated Aldehydes ◽  
Michael Acceptors

An asymmetric organocatalytic Michael addition–cyclization cascade reaction has been developed using cyclopentane-1,2-dione as a Michael donor and α,β-unsaturated aldehydes as Michael acceptors. Bicyclic hemiacetals were obtained in excellent yields and enantioselectivities. On the basis of the results, a one-pot reaction has been developed to obtain chiral 3-substituted cyclopentane-1,2-diones and substituted dihydropyrans in good yields and excellent enantioselectivity.

Uncatalyzed diastereoselective synthesis of alkyliminofurochromone-derived benzylmalononitriles via a three-component cascade reaction: competition between Diels–Alder cycloaddition and Michael addition

2021 ◽  
Author(s):  
Mohammad Bagher Teimouri ◽  
Zahra Mokhtare ◽  
Hamid Reza Khavasi
Keyword(s):  
Michael Addition ◽  
Heterocyclic Ring ◽  
Cascade Reaction ◽  
Diels Alder ◽  
Chemical Bonds ◽  
Diastereoselective Synthesis ◽  
Atom Economy ◽  
One Pot

Three new chemical bonds and three stereogenic centres and one heterocyclic ring were assembled stereoselectively in a convenient high atom-economy one-pot operation.

One-pot asymmetric synthesis of a hexahydrophenanthridine scaffold containing five stereocenters via an organocatalytic quadruple-cascade reaction

2021 ◽  
Author(s):  
Xiao-Long Zhang ◽  
Kai-Xiang Feng ◽  
Jian-Liang Hu ◽  
Qiao-Yu Shen ◽  
Wang-Sheng Huang ◽  
...  
Keyword(s):  
Asymmetric Synthesis ◽  
Cascade Reaction ◽  
One Pot ◽  
Unsaturated Aldehydes ◽  
Aldol Cyclization

An organocatalytic enantioselective aza-Michael-Michael-Michael/aldol cyclization quadruple-cascade reaction of 2-amino-β-nitrostyrenes and α,β-unsaturated aldehydes has been developed for the construction of fully substituted hexahydrophenanthridine.

scholarly journals Dearomative Michael addition involving enals and 2-nitrobenzofurans realized under NHC-catalysis

2022 ◽  
Author(s):  
Mateusz Dyguda ◽  
Anna Skrzyńska ◽  
Lesław Sieroń ◽  
Łukasz Albrecht
Keyword(s):  
Michael Addition ◽  
Unsaturated Aldehydes ◽  
Reaction Proceeds ◽  
Michael Acceptors ◽  
High Yields

In the manuscript the first enantioselective dearomative Michael addition between α,β-unsaturated aldehydes and 2-nitrobenzofurans realized under N-heterocyclic carbene activation has been described. The reaction proceeds via addition of homoenolate to Michael acceptors leading to the formation of biologically important heterocycles with high yields and stereoselectivities. Their functionalization potential has been confirmed in selected, diastereoselective transformations.

Solvent free one-pot multi-component synthesis of β-azaarene substituted ketones via a Sn-catalyzed C(sp3)–H functionalization of 2-alkylazaarenes

RSC Advances ◽  
2015 ◽  
Vol 5 (125) ◽  
pp. 103091-103094 ◽  
Author(s):  
Santosh S. Chavan ◽  
Mohsinkhan Y. Pathan ◽  
Shafeek A. R. Mulla
Keyword(s):  
Michael Addition ◽  
Cascade Reaction ◽  
Solvent Free ◽  
Efficient Synthesis ◽  
One Pot

A tin-catalyzed solvent free one-pot multi-component cascade reaction strategy for the efficient synthesis of β-azaarene substituted ketones via an aldol–Michael addition/C(sp3)–H functionalization of 2-alkylazaarenes has been developed.

One-pot synthesis of β-lactams by the Ugi and Michael addition cascade reaction

2018 ◽  
Vol 16 (33) ◽  
pp. 6096-6105 ◽  
Author(s):  
Xing Gao ◽  
Chunhui Shan ◽  
Zhihao Chen ◽  
Yan Liu ◽  
Xia Zhao ◽  
...  
Keyword(s):  
Michael Addition ◽  
Michael Reaction ◽  
Cascade Reaction ◽  
One Pot ◽  
Diversity Oriented Synthesis ◽  
Mild Conditions ◽  
One Pot Synthesis ◽  
Reaction Cascades

A diversity-oriented synthesis of β-lactams via Ugi/Michael reaction cascades under mild conditions was achieved.

Isocyanide-Based MCRs: Straightforward Access to Perfluroalkyl­ated γ-Spiroiminolactones

Synthesis ◽  
2018 ◽  
Vol 50 (20) ◽  
pp. 4104-4112 ◽  
Author(s):  
Hui Zhang ◽  
Weiguo Cao ◽  
Lili Tao ◽  
Zhenhua Fan ◽  
Xin Peng ◽  
...  
Keyword(s):  
Michael Addition ◽  
Nucleophilic Addition ◽  
Simple Procedure ◽  
Reaction Times ◽  
Cascade Reaction ◽  
One Pot ◽  
Excellent Chemical

A variety of perfluoroalkyl-substituted γ-spiroiminolactones have been synthesized via a one-pot, three-component cascade reaction in which isocyanides, methyl perfluoroalk-2-ynoates and 1,2-diketones undergo highly regioselective Michael addition, nucleophilic addition and cyclization. This reaction has the advantages of good to excellent chemical yields, operationally simple procedure, and short reaction times.

Enantioselective Michael Addition of Malonates to Enones

2020 ◽  
Vol 24 (7) ◽  
pp. 746-773
Author(s):  
Péter Bakó ◽  
Tamás Nemcsok ◽  
Zsolt Rapi ◽  
György Keglevich
Keyword(s):  
Michael Addition ◽  
Activity Relationship ◽  
Chalcone Derivatives ◽  
Michael Additions ◽  
Michael Reactions ◽  
Structure Activity ◽  
Cyclic Enones ◽  
Michael Acceptors ◽  
Relationship Of ◽  
Enantioselective Catalysts

: Many catalysts were tested in asymmetric Michael additions in order to synthesize enantioenriched products. One of the most common reaction types among the Michael reactions is the conjugated addition of malonates to enones making it possible to investigate the structure–activity relationship of the catalysts. The most commonly used Michael acceptors are chalcone, substituted chalcones, chalcone derivatives, cyclic enones, while typical donors may be dimethyl, diethyl, dipropyl, diisopropyl, dibutyl, di-tert-butyl and dibenzyl malonates. This review summarizes the most important enantioselective catalysts applied in these types of reactions.

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