Enantioselective Synthesis of O-Methoxycarbonyl Cyanohydrins: Chiral Building Blocks Generated by Bifunctional Catalysis with BINOLAM-AlCl.

ChemInform ◽  
2006 ◽  
Vol 37 (33) ◽  
Author(s):  
Alejandro Baeza ◽  
Jesus Casas ◽  
Carmen Najera ◽  
Jose M. Sansano ◽  
Jose M. Saa
Keyword(s):  
Building Blocks ◽  
Enantioselective Synthesis ◽  
Bifunctional Catalysis

Enantioselective Synthesis ofO-Methoxycarbonyl Cyanohydrins: Chiral Building Blocks Generated by Bifunctional Catalysis with BINOLAM-AlCl

2006 ◽  
Vol 2006 (8) ◽  
pp. 1949-1958 ◽  
Author(s):  
Alejandro Baeza ◽  
Jesús Casas ◽  
Carmen Nájera ◽  
José M. Sansano ◽  
José M. Saá
Keyword(s):  
Building Blocks ◽  
Enantioselective Synthesis ◽  
Bifunctional Catalysis

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 2,3-Dihydrofurans with Bifunctional Quinine/Squaramide Organocatalyst

2021 ◽  
Author(s):  
Zeynep Dilşad Susam ◽  
Merve Bozdemir ◽  
Gülsüm Gündoğdu ◽  
Cihangir Tanyeli
Keyword(s):  
Building Blocks ◽  
Enantioselective Synthesis ◽  
Dicarbonyl Compounds ◽  
Sn2 Reactions

Asymmetric organocatalytic domino type Michael-SN2 reactions give access to enantiomerically enriched dihydrofuran derivatives that can be used as valuable chiral building blocks. A variety of α-bromonitroalkenes and 1,3-dicarbonyl compounds were...

scholarly journals Acyl Transfer Strategies as Transient Activations for Enantioselective Synthesis

Synthesis ◽  
2019 ◽  
Vol 51 (09) ◽  
pp. 1923-1934 ◽  
Author(s):  
Jean Rodriguez ◽  
Adrien Quintard
Keyword(s):  
Ring Formation ◽  
Enantioselective Synthesis ◽  
The Other ◽  
Acyl Transfer ◽  
Bifunctional Catalysis ◽  
Innovative Methods ◽  
Subsequent Step ◽  
Transfer Strategies ◽  
Amine Function

In order to circumvent reactivity or selectivity issues associated with the addition of enolates to electrophiles, chemists have devised innovative methods involving transient activating groups. One of these powerful methods consists of the use of activated ketones, such as α-nitroketones, β-dicarbonyl compounds or β-ketosulfones, with electrophiles possessing a latent hydroxy or amine function. In the presence of a suitable catalyst, an enantioselective addition to the electrophile is facilitated triggering a subsequent Claisen-type fragmentation resulting in an acyl transfer. This subsequent step unveils the desired mono-activated function while directly transferring the ketone, forming in situ on the other side an ester or an amide.1 Introduction2 Intramolecular Acyl Transfer with Acyclic Substrates2.1 Bifunctional Catalysis2.2 Aminocatalysis3 Intermolecular Acyl Transfer with Acyclic Substrates4 Medium-Sized-Ring Formation with Cyclic Substrates5 Conclusion

scholarly journals Catalytic enantioselective synthesis of α-aryl α-hydrazino esters and amides

2020 ◽  
Vol 56 (43) ◽  
pp. 5823-5826
Author(s):  
Marta Velázquez ◽  
Saúl Alberca ◽  
Javier Iglesias-Sigüenza ◽  
Rosario Fernández ◽  
José M. Lassaletta ◽  
...  
Keyword(s):  
Building Blocks ◽  
Boronic Acids ◽  
Enantioselective Synthesis

Asymmetric 1,2-addition of aryl boronic acids to N-carbamoyl (Cbz and Fmoc) protected glyoxylate-derived hydrazones affords α-aryl α-hydrazino esters/amides, key building blocks en route to artificial peptides.

Enantioselective Synthesis of 1,3-Dioxygen-substituted Chiral Building Blocks

Synlett ◽  
1994 ◽  
Vol 1994 (03) ◽  
pp. 199-200 ◽  
Author(s):  
Chris H. Senanayake ◽  
Robert D. Larsen ◽  
Timothy J. Bill ◽  
Ji Liu ◽  
Edward G. Corley ◽  
...  
Keyword(s):  
Building Blocks ◽  
Enantioselective Synthesis

Recent Advances in the Synthesis of Enantiomerically Enriched Diaryl, Aryl Heteroaryl, and Diheteroaryl Alcohols through Addition of Organometallic Reagents to Carbonyl Compounds

Synthesis ◽  
2020 ◽  
Vol 52 (13) ◽  
pp. 1855-1873
Author(s):  
Senthil Narayanaperumal ◽  
Ricardo S. Schwab ◽  
Wystan K. O. Teixeira ◽  
Danilo Yano de Albuquerque
Keyword(s):  
Carbonyl Compounds ◽  
Building Blocks ◽  
Short Review ◽  
Biological Properties ◽  
Enantioselective Synthesis ◽  
Grignard Reagents ◽  
Organometallic Reagents ◽  
Important Family ◽  
Organolithium Reagents ◽  
Organozinc Reagents

Enantiomerically enriched diaryl, aryl heteroaryl, and dihetero­aryl alcohols are an important family of compounds known for their biological properties. Moreover, these molecules are highly privileged scaffolds used as building blocks for the synthesis of pharmaceutically relevant products. This short review provides background on the enantioselective arylation and heteroarylation of carbonyl compounds, as well as, the most significant improvements in this field with special emphasis on the application of organometallic reagents.1 Introduction2 Background on the Enantioselective Synthesis of Diaryl, Aryl Heteroaryl, and Diheteroaryl Alcohols3 Organozinc Reagents4 Organolithium Reagents5 Grignard Reagents6 Organoaluminum Reagents7 Organotitanium Reagents8 Organobismuth Reagents9 Miscellaneous10 Conclusion

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