Squaramide-catalysed asymmetric cascade aza-Michael/Michael addition reaction for the synthesis of chiral trisubstituted pyrrolidines

2015 ◽  
Vol 13 (46) ◽  
pp. 11351-11361 ◽  
Author(s):  
Bo-Liang Zhao ◽  
Ye Lin ◽  
Hao-Hao Yan ◽  
Da-Ming Du
Keyword(s):  
Michael Addition ◽  
Addition Reaction ◽  
Cascade Reaction ◽  
Michael Addition Reaction ◽  
Mild Conditions

A squaramide catalysed aza-Michael/Michael cascade reaction between nitroalkenes and tosylaminomethyl enones or enoates afforded highly functionalized chiral pyrrolidines in good yields (up to 99%) with good diastereoselectivities (up to 91 : 9 dr) and excellent enantioselectivities (up to >99% ee) under mild conditions.

Asymmetric synthesis of highly functionalized spirothiazolidinone tetrahydroquinolines via a squaramide-catalyzed cascade reaction

2018 ◽  
Vol 16 (48) ◽  
pp. 9390-9401 ◽  
Author(s):  
Yong-Xing Song ◽  
Da-Ming Du
Keyword(s):  
Asymmetric Synthesis ◽  
Michael Addition ◽  
Addition Reaction ◽  
Cascade Reaction ◽  
Michael Addition Reaction

A bifunctional squaramide-catalyzed asymmetric cascade aza-Michael/Michael addition reaction for the synthesis of chiral spirothiazolidinone tetrahydroquinolines with three contiguous stereocenters has been developed.

Molecular sieve mediated sequential Knoevenagel condensation/decarboxylative Michael addition reaction: efficient and mild conditions for the synthesis of 3,3-disubstituted oxindoles with an all carbon quaternary center

RSC Advances ◽  
2016 ◽  
Vol 6 (78) ◽  
pp. 74683-74690 ◽  
Author(s):  
Yi-Lin Guo ◽  
Yu-Hsun Li ◽  
Hsuan-Hao Chang ◽  
Ting-Shen Kuo ◽  
Jeng-Liang Han
Keyword(s):  
Michael Addition ◽  
Molecular Sieve ◽  
Addition Reaction ◽  
Knoevenagel Condensation ◽  
Michael Addition Reaction ◽  
Mild Conditions ◽  
Catalyst Free ◽  
Quaternary Center ◽  
Broad Scope

A mild, catalyst-free and efficient molecular sieve mediated sequential Knoevenagel condensation/decarboxylative Michael additon reaction has been developed. A broad scope of 3,3-disubstituted oxindoles were synthesized in good to excellent yields.

scholarly journals Imidazolyl activated carbon refluxed with ethanediamine as reusable heterogeneous catalysts for Michael addition

RSC Advances ◽  
2019 ◽  
Vol 9 (1) ◽  
pp. 185-191
Author(s):  
Wenzhu Liu ◽  
Jiafu Xiao ◽  
Qiong Xu ◽  
Xianxiang Liu ◽  
Sheng Zhong ◽  
...  
Keyword(s):  
Activated Carbon ◽  
Michael Addition ◽  
Heterogeneous Catalysts ◽  
Addition Reaction ◽  
Catalytic Performance ◽  
Michael Addition Reaction ◽  
Mild Conditions ◽  
Excellent Catalytic Performance

Imidazolyl activated carbon was prepared under mild conditions and showed excellent catalytic performance in Michael addition reaction.

Novel Brønsted Acidic Ionic Liquids Based on Benzimidazolium Cation: Synthesis and Catalyzed Conjugate Addition of Indoles with α,β-unsaturated Ketones

2011 ◽  
Vol 233-235 ◽  
pp. 977-984
Author(s):  
Bin Wang ◽  
Chen Jiang Liu
Keyword(s):  
Ionic Liquids ◽  
Michael Addition ◽  
Addition Reaction ◽  
Conjugate Addition ◽  
Michael Addition Reaction ◽  
Unsaturated Ketones ◽  
Mild Conditions ◽  
Acidic Ionic Liquids ◽  
High Yields ◽  
The Michael Addition

Brønsted acidic ionic liquids based on benzimidazolium cation was synthesized and employed as an efficient catalysts for the Michael addition reaction of indoles to α,β-unsaturated ketones under mild conditions to afford the corresponding conjugate addition products in high yields (90%-98%). The catalyst 1-butyl-3-(3-sulfopropyl)benzimidazolium p-toluenesulfonate ([PSbbim][p-CH3PhSO3]) could be reused at least three times without a noticeably decrease in its activity.

Cupin Variants as Macromolecular Ligand Library for Stereoselective Michael Addition of Nitroalkanes

2019 ◽  
Author(s):  
Nobutaka Fujieda ◽  
Miho Yuasa ◽  
Yosuke Nishikawa ◽  
Genji Kurisu ◽  
Shinobu Itoh ◽  
...  
Keyword(s):  
Michael Addition ◽  
In Silico ◽  
Addition Reaction ◽  
Single Point ◽  
Point Mutations ◽  
Unsaturated Ketone ◽  
Michael Addition Reaction ◽  
Beta Barrel ◽  
Cupin Superfamily ◽  
Single Point Mutations

Cupin superfamily proteins (TM1459) work as a macromolecular ligand framework with a double-stranded beta-barrel structure ligating to a Cu ion through histidine side chains. Variegating the first coordination sphere of TM1459 revealed that H52A and H54A/H58A mutants effectively catalyzed the diastereo- and enantio-selective Michael addition reaction of nitroalkanes to an α,β-unsaturated ketone. Moreover, in silico substrate docking signified C106N and F104W single-point mutations, which inverted the diastereoselectivity of H52A and further improved the stereoselectivity of H54A/H58A, respectively.

Tandem Alkylation/Michael Addition Reaction of Dithiocarbamic Acids with Alkyl γ-Bromocrotonates: Access to Functionalized 1,3-Thiazolidine-2-thiones

Synthesis ◽  
2021 ◽  
Author(s):  
Azim Ziyaei Halimehjani ◽  
Petr Beier ◽  
Maryam Khalili Foumeshi ◽  
Ali Alaei ◽  
Blanka Klepetářová
Keyword(s):  
Amino Acids ◽  
Carbon Disulfide ◽  
Multicomponent Reaction ◽  
Michael Addition ◽  
Addition Reaction ◽  
Primary Amines ◽  
Oxidation Reactions ◽  
Michael Addition Reaction ◽  
Synthetic Utility ◽  
Reaction Proceeds

AbstractThiazolidine-2-thiones were prepared via a novel multicomponent reaction of primary amines (amino acids), carbon disulfide, and γ-bromocrotonates. The reaction proceeds via a domino alkylation/intramolecular Michael addition to provide the corresponding thiazolidine-2-thiones in high to excellent yields. By using diamines in this protocol, bis(thiazolidine-2-thiones) derivatives were synthesized. The synthetic utility of the adducts was demonstrated by hydrolysis, amidation, and oxidation reactions.

Bisphosphine catalyzed sequential [3 + 2] cycloaddition and Michael addition of ynones with benzylidenepyrazolones via dual α′,α′-C(sp3)–H bifunctionalization to construct cyclopentanone-fused spiro-pyrazolones

2018 ◽  
Vol 16 (48) ◽  
pp. 9461-9471 ◽  
Author(s):  
Jiayong Zhang ◽  
Zhiwei Miao
Keyword(s):  
Michael Addition ◽  
Addition Reaction ◽  
Michael Addition Reaction

A sequential [3 + 2] cycloaddition and Michael addition reaction of ynones with benzylidenepyrazolones afforded cyclopentanone-fused spiro-pyrazolones catalyzed by DPPB via dual α′,α′-C(sp3)–H bifunctionalization.

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