scholarly journals Construction of highly enantioenriched spirocyclopentaneoxindoles containing four consecutive stereocenters via thiourea-catalyzed asymmetric Michael–Henry cascade reactions

2017 ◽  
Vol 13 ◽  
pp. 1342-1349 ◽  
Author(s):  
Yonglei Du ◽  
Jian Li ◽  
Kerong Chen ◽  
Chenglin Wu ◽  
Yu Zhou ◽  
...  
Keyword(s):  
Asymmetric Synthesis ◽  
Functional Groups ◽  
Cascade Reactions ◽  
Atom Economy ◽  
Operational Simplicity

The thiourea-catalyzed asymmetric synthesis of highly enantioenriched spirocyclopentaneoxindoles containing chiral amide functional groups using simple 3-substituted oxindoles and nitrovinylacetamide as starting materials was achieved successfully. This protocol features operational simplicity, high atom economy, and high catalytic asymmetry, thus representing a versatile approach to the synthesis of highly enantioenriched spirocyclopentaneoxindoles.

Asymmetric Synthesis of Fused Tetrahydroquinolines via Intramolecular Aza-Diels-Alder Reaction of ortho-Quinone Methide Imines

Synthesis ◽  
2021 ◽  
Author(s):  
Fabian Hofmann ◽  
Cornelius Gärtner ◽  
Martin Kretzschmar ◽  
Christoph Schneider
Keyword(s):  
Asymmetric Synthesis ◽  
Alder Reaction ◽  
Single Step ◽  
Diels Alder ◽  
Quinone Methide ◽  
Bronsted Acid ◽  
Atom Economy ◽  
Diels Alder Reaction ◽  
Brönsted Acid ◽  
Chiral Bronsted Acid

Aza-Diels Alder reactions are straightforward processes in the construction of N-heterocycles, featuring inherent atom-economy and stereospecificity. Intramolecular strategies allow formation of bicyclic core structures with up to three stereocenters within a single step. Herein, this concept is combined with the chemistry of chiral Brønsted acid-bound ortho-quinone methide imines generating a range of interesting fused tetrahydro-quinolines in a diastereo- and enantioselective manner.

Facile Approach to Geminal Heterodihalogenation. One-Pot Synthesis of α-Bromo-α-Chloro Ketones

Synlett ◽  
2020 ◽  
Vol 31 (14) ◽  
pp. 1430-1434
Author(s):  
Ming Bian ◽  
Jin-feng Zhou ◽  
Dong-min Tang
Keyword(s):  
Drug Discovery ◽  
Dimethyl Sulfoxide ◽  
Functional Groups ◽  
Methyl Ketones ◽  
One Pot ◽  
One Pot Synthesis ◽  
Operational Simplicity

An efficient and practical protocol for the geminal heterodihalogenation of methyl ketones by using readily available dimethyl sulfoxide and a combination of HCl and HBr is reported. Control experiments suggested that the acidity of the solution, as well as the oxidizing ability and nucleophilicity of the dimethyl sulfoxide might work cooperatively in ensuring the success of the tandem substitution. Its operational simplicity, easy accessibility, and mild oxidative conditions suggest that the present strategy might be useful for the assembly of bromochloromethyl functional groups in drug discovery.

scholarly journals Asymmetric synthesis of 2,5-dissubstituded pyrrolidines through cascade reactions

2020 ◽  
Author(s):  
Paulo Gabriel Massayuki Miyake Nakaya ◽  
Anita Jocelyne Marsaioli ◽  
Fábio Domingues Nasário
Keyword(s):  
Asymmetric Synthesis ◽  
Cascade Reactions

scholarly journals P(III) vs. P(V): A P(V) Reagent for Thiophosphoramidate Linkages and Application to An Asymmetric Synthesis of a Cyclic Dinucleotide STING Agonist

2021 ◽  
Author(s):  
Bin Zheng ◽  
Chao Hang ◽  
Jason Zhu ◽  
Geoffrey Purdum ◽  
Melda Sezen-Edmonds ◽  
...  
Keyword(s):  
Asymmetric Synthesis ◽  
Functional Groups ◽  
Stereoselective Synthesis ◽  
Key Functional Groups ◽  
First Time ◽  
Cyclic Dinucleotide

A highly stereoselective synthesis of a cyclic dinucleotide (CDN) STING agonist containing two chiral thiophosphoramidate linkages is described. These rare, yet key functional groups were, for the first time, installed efficiently and with high diastereoselectivity using a specially designed P(V) reagent. By utilizing this strategy, the CDN was prepared in greater than sixteen-fold higher yield than the prior P(III) approach, with fewer hazardous reagents and chromatographic purifications.

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