ChemInform Abstract: Michael Addition Reaction: Applications in Total Synthesis of Bioactive Natural Products

The first total synthesis of kukoamine B bimesylate was completed from 1,4-diaminobutane dihydrochloride in 12 steps with a 11.4% overall yield, and all the steps could be carried out at a kilogram scale. The cyano groups were used as the precursor of amino groups to avoid the competitive reaction delicately. The aza-Michael addition reaction, amidation and hydrogenation of the cyano group sequence was streamlined as a general approach towards the synthesis of polyamine structures.

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Asymmetric total synthesis of (+)-asenapine

Organic & Biomolecular Chemistry ◽

10.1039/c9ob00178f ◽

2019 ◽

Vol 17 (12) ◽

pp. 3225-3231 ◽

Cited By ~ 2

Author(s):

Piotr Szcześniak ◽

Olga Staszewska-Krajewska ◽

Jacek Mlynarski

Keyword(s):

Total Synthesis ◽

Michael Addition ◽

Addition Reaction ◽

Reductive Cyclization ◽

Michael Addition Reaction ◽

Asymmetric Total Synthesis ◽

Key Steps

Asymmetric total synthesis of (+)-asenapine involving the organocatalytic Michael addition reaction and subsequent Zn-promoted reductive cyclization as the key steps.

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ChemInform Abstract: Tandem N-Acyliminium Michael Addition Reaction. An Efficient Total Synthesis of the Quinolizidine Alkaloids (.+-.)-Myrtine and (.+-.)- Lasubine II.

ChemInform ◽

10.1002/chin.199339286 ◽

2010 ◽

Vol 24 (39) ◽

pp. no-no

Author(s):

R. A. PILLI ◽

L. C. DIAS ◽

A. O. MALDANER

Keyword(s):

Total Synthesis ◽

Michael Addition ◽

Addition Reaction ◽

Quinolizidine Alkaloids ◽

Michael Addition Reaction

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Computational studies on geopolymer catalyst for Michael addition reaction

10.1021/scimeetings.0c05563 ◽

2020 ◽

Author(s):

Uppari Naveena

Keyword(s):

Michael Addition ◽

Addition Reaction ◽

Computational Studies ◽

Michael Addition Reaction

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

10.26434/chemrxiv.11481834.v1 ◽

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.

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

Synthesis ◽

10.1055/a-1372-1619 ◽

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.

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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

Organic & Biomolecular Chemistry ◽

10.1039/c8ob02675k ◽

2018 ◽

Vol 16 (48) ◽

pp. 9461-9471 ◽

Cited By ~ 2

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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