scholarly journals Interrupted Curtius Rearrangements of Quaternary Proline Derivatives: A Flow Route to Acyclic Ketones and Unsaturated Pyrrolidines

2021 ◽  
Author(s):  
Marcus Baumann ◽  
Thomas S. Moody ◽  
Megan Smyth ◽  
Scott Wharry
Keyword(s):  
Proline Derivatives ◽  
Acyclic Ketones

Synthesis of some proline derivatives by means of michael additions of glycine esters

1991 ◽  
Vol 32 (30) ◽  
pp. 3727-3730 ◽  
Author(s):  
Anne van der Werf ◽  
Richard M. Kellogg
Keyword(s):  
Michael Additions ◽  
Proline Derivatives

Synthetic Studies onl-Proline and (4 R )-Hydroxy-l-proline Derivatives

Synthesis ◽  
2004 ◽  
Vol 2004 (08) ◽  
pp. 1171-1182 ◽  
Author(s):  
Cristina Minguillón ◽  
Teresa González ◽  
Olga Abad ◽  
M. Carmen Santano
Keyword(s):  
Synthetic Studies ◽  
Proline Derivatives

scholarly journals Enantioselective addition of diethylzinc to benzaldehyde over mesoporous SBA-15 functionalized with chiral proline derivatives

2009 ◽  
Vol 359 (1-2) ◽  
pp. 96-107 ◽  
Author(s):  
Li-Hsiu Hsiao ◽  
Shih-Yuan Chen ◽  
Shing-Jong Huang ◽  
Shang-Bin Liu ◽  
Peng-Huan Chen ◽  
...  
Keyword(s):  
Enantioselective Addition ◽  
Proline Derivatives

Reduction of chiral acyclic ketones with hydride-transfer agents. Semiempirical analysis of the observed stereoselectivity

1988 ◽  
pp. 101-105 ◽  
Author(s):  
Carlos Alvarez Ibarra ◽  
Rafael Pérez-Ossorio ◽  
Maria L. Quiroga ◽  
Maria S. Arias Pérez ◽  
Maria J. Fernández Dominguez
Keyword(s):  
Hydride Transfer ◽  
Acyclic Ketones ◽  
Transfer Agents

ChemInform Abstract: Synthesis of Polysubstituted Pyrrolizidines from Proline Derivatives and Conjugated Nitroolefins.

ChemInform ◽  
2010 ◽  
Vol 28 (44) ◽  
pp. no-no
Author(s):  
F. FELLUGA ◽  
G. PITACCO ◽  
C. VISINTIN ◽  
E. VALENTIN
Keyword(s):  
Proline Derivatives

scholarly journals Pyrrolidine in Drug Discovery: A Versatile Scaffold for Novel Biologically Active Compounds

2021 ◽  
Vol 379 (5) ◽  
Author(s):  
Giovanna Li Petri ◽  
Maria Valeria Raimondi ◽  
Virginia Spanò ◽  
Ralph Holl ◽  
Paola Barraja ◽  
...  
Keyword(s):  
Three Dimensional ◽  
Binding Mode ◽  
Biologically Active ◽  
Bioactive Molecules ◽  
Biological Profile ◽  
Pyrrolidine Ring ◽  
Reaction Conditions ◽  
Drug Candidates ◽  
Steric Factors ◽  
Proline Derivatives

AbstractThe five-membered pyrrolidine ring is one of the nitrogen heterocycles used widely by medicinal chemists to obtain compounds for the treatment of human diseases. The great interest in this saturated scaffold is enhanced by (1) the possibility to efficiently explore the pharmacophore space due to sp3-hybridization, (2) the contribution to the stereochemistry of the molecule, (3) and the increased three-dimensional (3D) coverage due to the non-planarity of the ring—a phenomenon called “pseudorotation”. In this review, we report bioactive molecules with target selectivity characterized by the pyrrolidine ring and its derivatives, including pyrrolizines, pyrrolidine-2-one, pyrrolidine-2,5-diones and prolinol described in the literature from 2015 to date. After a comparison of the physicochemical parameters of pyrrolidine with the parent aromatic pyrrole and cyclopentane, we investigate the influence of steric factors on biological activity, also describing the structure–activity relationship (SAR) of the studied compounds. To aid the reader’s approach to reading the manuscript, we have planned the review on the basis of the synthetic strategies used: (1) ring construction from different cyclic or acyclic precursors, reporting the synthesis and the reaction conditions, or (2) functionalization of preformed pyrrolidine rings, e.g., proline derivatives. Since one of the most significant features of the pyrrolidine ring is the stereogenicity of carbons, we highlight how the different stereoisomers and the spatial orientation of substituents can lead to a different biological profile of drug candidates, due to the different binding mode to enantioselective proteins. We believe that this work can guide medicinal chemists to the best approach in the design of new pyrrolidine compounds with different biological profiles.

Enantioselective addition of diethylzinc to aldehydes catalyzed by 5-cis-substituted proline derivatives

Tetrahedron ◽  
2019 ◽  
Vol 75 (1) ◽  
pp. 94-101 ◽  
Author(s):  
Felix Prause ◽  
Stefan Wagner ◽  
Matthias Breuning
Keyword(s):  
Enantioselective Addition ◽  
Proline Derivatives
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