Asymmetric total synthesis of (+)-asenapine

2019 ◽  
Vol 17 (12) ◽  
pp. 3225-3231 ◽  
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.

The Total Synthesis of Spermine Alkaloid Kukoamine Bimesylate

Synlett ◽  
2018 ◽  
Vol 29 (20) ◽  
pp. 2669-2672
Author(s):  
Kai Dong
Keyword(s):  
Total Synthesis ◽  
Michael Addition ◽  
Addition Reaction ◽  
Cyano Group ◽  
Michael Addition Reaction ◽  
Amino Groups ◽  
Competitive Reaction ◽  
12 Steps ◽  
Cyano Groups

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.

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
Sign in / Sign up

Export Citation Format

Share Document