Synthesis
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Updated Thursday, 02 December 2021

Synthesis ◽  
2021 ◽  
Author(s):  
Hetti Handi Chaminda Lakmal ◽  
Jacob Istre ◽  
Xiaolin Qian ◽  
Hui Zhou ◽  
Henry U Valle ◽  
...  

Chemo-switchable catalytic [2+2+2] cycloaddition of alkenes with formaldimines has been reported. Bis(tosylamido)methane (BTM) and 1,2-ditosyl-1,2-diazetidine (DTD), two bench-stable precursors for highly reactive tosylformaldimine, have been identified to be effective. BTM worked as a selective releaser of the formaldimine for catalytic [2+2+2] reactions toward hexahydropyrimidine products via a presumable “imine-alkene-imine” addition. A unique catalytic retro-[2+2] reaction of DTD was used and has enabled a proposed “imine-alkene-alkene” pathway with high chemoselectivity for the synthesis of 2,4-diarylpyperidine derivatives. The two alternative processes were catalyzed by simple and environmentally benign catalysts InCl3 and FeBr2, respectively.


Synthesis ◽  
2021 ◽  
Author(s):  
David Whalley ◽  
Michael Greaney

The Smiles rearrangement has undergone a renaissance in recent years providing new avenues for non-canonical arylation techniques in both the radical and polar regimes. This Short Review will discuss recent applications of the reaction (from 2017 onwards), including its relevance to areas such as heterocycle synthesis, functionalisation of alkenes and alkynes as well as glimpses at new directions for the field.


Synthesis ◽  
2021 ◽  
Author(s):  
Travis Hammerstad ◽  
Pooja V. Hegde ◽  
Kathleen J. Wang ◽  
Courtney Aldrich

A convenient procedure for the chemoselective reduction of tertiary amides at room temperature in the presence of air and moisture using 1,3-diphenyldisiloxane (DPDS) has been developed. The reaction conditions are tolerant of a great number of functional groups including esters, nitriles, secondary amides, carbamates, sulfoxides, sulfones, sulfonyl fluorides, halogens, aryl-nitro groups, and arylamines. The conditions reported are the mildest to date and utilize EtOAc, a preferred solvent given its excellent safety profile and lower environmental impact. The ease of set up and broad chemoselectivity make this method attractive for organic synthesis. These results further demonstrate the utility of DPDS as a selective reducing agent.


Synthesis ◽  
2021 ◽  
Author(s):  
Olivier Monasson ◽  
Maciej Malinowski ◽  
Nadége Lubin-Germnain ◽  
Angélique Ferry

A range of C2-phosphonylated sugars have been accessed through a palladium-catalyzed Hirao cross-coupling on 2-iodoglycals using trialkylphosphites as phosphorylating reagents. The developed conditions led to create an unnatural C-P bond on sugars and proved to be compatible with diversely protected glycals (acetyl-, benzyl-, PMB-protected) as well as with unprotected substrates. Several monosaccharides and one disaccharide have been synthesized by this methodology. Deprotection conditions were also described.


Synthesis ◽  
2021 ◽  
Author(s):  
Yunfei Du ◽  
Xiaoxian Li ◽  
Beibei Zhang ◽  
Zhenyang Yu ◽  
Dongke Zhang ◽  
...  

AbstractThe reaction of N-arylpropynamides with (dichloroiodo)benzene (PhICl2) and diselenides/disulfides resulted in a divergent synthesis of chalcogenylated quinolinones and spiro[4.5]trienes through intramolecular electrophilic cyclization and chalcogenylation. The chalcogenyl functional group was introduced by an electrophilic reactive organosulfenyl chloride or selenenyl chloride species, generated in situ from the reaction of disulfides/diselenides and PhICl2. Notably, the divergent cyclization pathways were determined by the substituent type on the aniline ring in N-arylpropynamide substrates. Substrates bearing a fluoro, methoxy or trifluoromethoxy group at the para-position of the aniline underwent an alternative spiralization pathway to give the 3-chalcogenylated spiro[4,5]trienones.


Synthesis ◽  
2021 ◽  
Author(s):  
Nittaya Wiriya ◽  
Mookda Pattarawarapan ◽  
Saranphong Yimklan ◽  
Surat Hongsibsong ◽  
Wong Phakhodee

Indoloquinazolines functionalized at C-12 which are structure analogs of the natural alkaloid cephalanthrin B were readily constructed via a Ph3P-I2 mediated one-pot reaction of isatins with aromatic alcohols. In the presence of excess phenols, the C-12 aryloxy ester products were afforded in moderate to good yields under mild conditions. Moreover, fused bicyclic hydroxyaryl derivatives such as 8-hydroxyquinoline gave rise to novel C-12 spiro-γ-lactone derivatives. Reactive iminium cation species derived from dehydration of the C-12 hydroxy ester precursor is proposed to be transient intermediates responsible for these unprecedented transformations.


Synthesis ◽  
2021 ◽  
Author(s):  
Prasanjit Ghosh ◽  
Swati Lekha Mondal ◽  
Mahiuddin Baidya

The N–O heterocycles are biologically relevant scaffolds and versatile building blocks in contemporary organic synthesis. In this short review, we effort to showcase the involvement and elevation of various cycloaddition strategies towards the production of N–O heterocycles 1,2-oxazines, 1,2-oxazepanes, and 1,2-oxazetidines. A blueprint of advantages and challenges associated with these synthetic endeavors is provided.


Synthesis ◽  
2021 ◽  
Author(s):  
Jean-François Paquin ◽  
Xavier Bertrand ◽  
Pascal Paquin ◽  
Laurent Chabaud

AbstractThe hydrochlorination, hydrobromination, and hydroiodination of unactivated alkenes using methanesulfonic acid and inorganic halide salts (CaCl2, LiBr, LiI) in acetic acid are reported. This approach uses readily available and inexpensive reagents to provide the alkyl halides in up to 99% yield. An example of deuteriochlorination using deuterated acetic acid as the solvent is also demonstrated.


Synthesis ◽  
2021 ◽  
Author(s):  
Corinna S Schindler ◽  
Lara Cala ◽  
Mario A Gaviria ◽  
Scott L Kim ◽  
Trenton R Vogel

The design of concise and efficient synthetic strategies to access naturally occurring, pharmaceutically active complex molecules is of utmost importance in current chemistry. It not only enables rapid access to these molecules and their analogues but also provides sufficient quantities for their biological evaluation. Identification of any symmetric or pseudosymmetric synthetic intermediates upon retrosynthetic bond disconnection of the target molecule holds the promise to significantly streamline the route towards the compound of interest. This review will highlight recent examples of successful natural product syntheses reported within the past five years that benefited from the recognition of symmetry elements during the retrosynthetic design.


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