Enantioselective Synthesis of Chiral Isotopomers of 1-Alkanols by a ZACA-Cu-Catalyzed Cross-Coupling Protocol

2014 ◽  
Vol 20 (49) ◽  
pp. 16060-16064 ◽  
Author(s):  
Shiqing Xu ◽  
Akimichi Oda ◽  
Ei-ichi Negishi
Keyword(s):  
Cross Coupling ◽  
Enantioselective Synthesis

Enantioselective Synthesis of Azamerone

2018 ◽  
Author(s):  
Matthew L. Landry ◽  
Grace McKenna ◽  
Noah Burns
Keyword(s):  
Late Stage ◽  
Cross Coupling ◽  
Enantioselective Synthesis ◽  
Selective Synthesis

A concise and selective synthesis of the dichlorinated meroterpenoid azamerone is described. The paucity of tactics for the synthesis of chiral organochlorides motivated the development of unique strategies for accessing these motifs in enantioenriched forms. The route features a novel enantioselective chloroetherification reaction, a Pd-catalyzed cross-coupling between a quinone diazide and a boronic hemiester, and a late-stage tetrazine [4+2]-cycloaddition/oxidation cascade.

Modular, Stereocontrolled Cβ–H/Cα–C Activation of Alkyl Carboxylic Acids

2019 ◽  
Author(s):  
Ming Shang ◽  
Karla S. Feu ◽  
Julien C. Vantourout ◽  
Lisa M. Barton ◽  
Heather L. Osswald ◽  
...  
Keyword(s):  
Carboxylic Acid ◽  
Heterocyclic Compounds ◽  
Cross Coupling ◽  
Building Blocks ◽  
Enantioselective Synthesis ◽  
Carbon Centers ◽  
Drug Candidates ◽  
Rapid Diversification ◽  
Directing Group ◽  
Compound Series

<div> <div> <div> <p>The union of two powerful transformations, directed C–H activation and decarboxylative cross-coupling, for the enantioselective synthesis of vicinally functionalized alkyl, carbocyclic, and heterocyclic compounds is described. Starting from simple carboxylic acid building blocks, this modular sequence exploits the residual directing group to access more than 50 scaffolds that would be otherwise extremely difficult to prepare. The tactical use of these two transformations accomplishes a formal vicinal difunctionalization of carbon centers in a way that is modular and thus amenable to rapid diversity incorporation. A simplification of routes to known preclinical drug candidates is presented along with the rapid diversification of an antimalarial compound series. </p> </div> </div> </div>

Enantioselective Synthesis of Azamerone

2018 ◽  
Author(s):  
Matthew L. Landry ◽  
Grace McKenna ◽  
Noah Burns
Keyword(s):  
Late Stage ◽  
Cross Coupling ◽  
Enantioselective Synthesis ◽  
Selective Synthesis

A concise and selective synthesis of the dichlorinated meroterpenoid azamerone is described. The paucity of tactics for the synthesis of chiral organochlorides motivated the development of unique strategies for accessing these motifs in enantioenriched forms. The route features a novel enantioselective chloroetherification reaction, a Pd-catalyzed cross-coupling between a quinone diazide and a boronic hemiester, and a late-stage tetrazine [4+2]-cycloaddition/oxidation cascade.

ChemInform Abstract: Enantioselective Synthesis of 4-Substituted Phenylalanines by Cross-Coupling Reactions.

ChemInform ◽  
2010 ◽  
Vol 30 (16) ◽  
pp. no-no
Author(s):  
Fariborz Firooznia ◽  
Candido Gude ◽  
Kenneth Chan ◽  
Nicholas Marcopulos ◽  
Yoshitaka Satoh
Keyword(s):  
Cross Coupling ◽  
Enantioselective Synthesis ◽  
Coupling Reactions ◽  
Cross Coupling Reactions

Enantioselective synthesis of ( R )‐Cinacalcet via cobalt‐catalysed asymmetric Negishi cross‐coupling

Chirality ◽  
2019 ◽  
Vol 31 (9) ◽  
pp. 682-687 ◽  
Author(s):  
Xiao Sun ◽  
Xueyang Wang ◽  
Feipeng Liu ◽  
Zidong Gao ◽  
Qinghua Bian ◽  
...  
Keyword(s):  
Cross Coupling ◽  
Enantioselective Synthesis

A Concise Enantioselective Synthesis of (S)-Preclamol via Asymmetric Catalytic Negishi Cross-Coupling Reaction

Synlett ◽  
2019 ◽  
Vol 30 (07) ◽  
pp. 860-862 ◽  
Author(s):  
Yun Zhou ◽  
Chunxiao Liu ◽  
Lifeng Wang ◽  
Leng Han ◽  
Shicong Hou ◽  
...  
Keyword(s):  
Total Yield ◽  
Coupling Reaction ◽  
Cross Coupling ◽  
Enantioselective Synthesis ◽  
Synthetic Approach ◽  
Chiral Drugs ◽  
Asymmetric Catalytic ◽  
Cross Coupling Reaction ◽  
Tertiary Carbon ◽  
Key Steps

A novel, concise, and efficient enantioselective synthesis of (S)-preclamol (87% ee, 51% total yield) has been developed. The key steps of this synthetic approach included cobalt-catalyzed asymmetric catalytic cross-coupling of α-bromo ester with arylzinc and the reduction of chiral ester to diol with a tertiary carbon atom. Moreover, it was demonstrated that our enantioselective Negishi cross-coupling was a powerful tool to construct stereogenic benzylmethyl center in chiral drugs on a gram scale.

scholarly journals An enantioselective synthesis of the C24–C40 fragment of (−)-pulvomycin

2014 ◽  
Vol 50 (38) ◽  
pp. 4901-4903 ◽  
Author(s):  
Sandra Börding ◽  
Thorsten Bach
Keyword(s):  
Synthesis Method ◽  
Cross Coupling ◽  
Enantioselective Synthesis ◽  
Pure Form ◽  
Enantiomerically Pure ◽  
Diastereoselective Addition ◽  
Key Steps

The C24–C40 fragment of (−)-pulvomycin was prepared in enantiomerically pure form using a concise synthesis method (15 linear steps from d-fucose, 6.8% overall yield) featuring a diastereoselective addition to an aldehyde, a β-selective glycosylation and a Stille cross-coupling as the key steps.

ChemInform Abstract: Enantioselective Synthesis and Cross-Coupling of Tertiary Propargylic Boronic Esters Using Lithiation-Borylation of Propargylic Carbamates.

ChemInform ◽  
2013 ◽  
Vol 44 (15) ◽  
pp. no-no
Author(s):  
Benjamin M. Partridge ◽  
Laetitia Chausset-Boissarie ◽  
Matthew Burns ◽  
Alexander P. Pulis ◽  
Varinder K. Aggarwal
Keyword(s):  
Cross Coupling ◽  
Enantioselective Synthesis ◽  
Boronic Esters

ChemInform Abstract: Diastereo- and Enantioselective Synthesis of 1,2-Diols by Vanadium(II) Promoted Pinacol Cross Coupling.

ChemInform ◽  
2010 ◽  
Vol 22 (44) ◽  
pp. no-no
Author(s):  
R. ANNUNZIATA ◽  
M. CINQUINI ◽  
F. COZZI ◽  
P. GIARONI ◽  
M. BENAGLIA
Keyword(s):  
Cross Coupling ◽  
Enantioselective Synthesis
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