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.

Diastereoselective synthesis of pitavastatin calcium via bismuth-catalyzed two-component hemiacetal/oxa-Michael addition reaction

2015 ◽  
Vol 13 (38) ◽  
pp. 9813-9819 ◽  
Author(s):  
Fangjun Xiong ◽  
Haifeng Wang ◽  
Lingjie Yan ◽  
Lingjun Xu ◽  
Yuan Tao ◽  
...  
Keyword(s):  
Asymmetric Synthesis ◽  
Michael Addition ◽  
Addition Reaction ◽  
Diastereoselective Synthesis ◽  
Michael Addition Reaction ◽  
Two Component ◽  
Pitavastatin Calcium

An efficient and concise asymmetric synthesis of pitavastatin calcium (1) starting from commercially available (S)-epichlorohydrin is described.

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.

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.

ChemInform Abstract: Organocatalyzed Michael Addition Reaction by Novel (2R,3aS,7aS)-Octahydroindole-2-carboxylic Acid, a New Fused Proline.

ChemInform ◽  
2011 ◽  
Vol 42 (21) ◽  
pp. no-no
Author(s):  
David Roca-Lopez ◽  
Pedro Merino ◽  
Francisco J. Sayago ◽  
Carlos Cativiela ◽  
Raquel P. Herrera
Keyword(s):  
Carboxylic Acid ◽  
Michael Addition ◽  
Addition Reaction ◽  
Michael Addition Reaction

TiO2 nano crystallites catalyzed water mediated microwave assisted regioselective three component domino hydrolysis/aldol condensation/Michael addition reaction of 3-(1,5-dioxo-1,5-diphenylpentan-3-yl)quinolin-2(1H)-one

RSC Advances ◽  
2014 ◽  
Vol 4 (100) ◽  
pp. 57016-57025 ◽  
Author(s):  
Eethamukkala Ubba ◽  
Fazlur-Rahman Nawaz Khan ◽  
Euh Duck Jeong ◽  
Eun Hyuk Chung
Keyword(s):  
Michael Addition ◽  
Addition Reaction ◽  
Aldol Condensation ◽  
Michael Addition Reaction ◽  
Microwave Assisted ◽  
Nano Crystalline

Microwave supported, water intervened, nano crystalline TiO2 catalyzed synthesis of 3-(1,5-dioxo-1,5-diphenylpentan-3-yl)quinolin-2(1H)-ones, is described.

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