Oxazolidinone cross-alkylation during Evans’ asymmetric alkylation reaction

Tetrahedron ◽  
2011 ◽  
Vol 67 (47) ◽  
pp. 9104-9111 ◽  
Author(s):  
Nieves Fresno ◽  
Ruth Pérez-Fernández ◽  
Pilar Goya ◽  
Ma Luisa Jimeno ◽  
Ibón Alkorta ◽  
...  
Keyword(s):  
Alkylation Reaction ◽  
Asymmetric Alkylation

scholarly journals Applications of oxazolidinones as chiral auxiliaries in the asymmetric alkylation reaction applied to total synthesis

RSC Advances ◽  
2016 ◽  
Vol 6 (36) ◽  
pp. 30498-30551 ◽  
Author(s):  
Majid M. Heravi ◽  
Vahideh Zadsirjan ◽  
Behnaz Farajpour
Keyword(s):  
Total Synthesis ◽  
Alkylation Reaction ◽  
Chiral Auxiliaries ◽  
Asymmetric Alkylation

In this review, a number of applications of chiral oxazolidinones in the asymmetric alkylation reaction applied to total synthesis are described.

Ephedrines as Chiral Auxiliaries in Enantioselective Alkylation Reactions of Acyl Ephedrine Amides and Esters: A Review

2018 ◽  
Vol 15 (1) ◽  
pp. 38-83 ◽  
Author(s):  
Alejandro Cruz ◽  
Itzia I. Padilla-Martínez ◽  
Maria E. Bautista-Ramirez
Keyword(s):  
Asymmetric Synthesis ◽  
Bond Formation ◽  
Alkyl Halides ◽  
Aldol Reactions ◽  
Alkylation Reaction ◽  
Chiral Auxiliaries ◽  
Asymmetric Alkylation ◽  
Chiral Compounds ◽  
High Yields ◽  
Alkylation Reactions

Background: In modern chemistry, the asymmetric synthesis for the preparation of high purity chiral compounds to be used as pharmaceuticals or additives in foods have been of capital importance. Chiral auxiliary reagents are used to control the stereochemistry of the reaction in the generation of new chiral compounds, in this context, Ephedra compounds (ephedrines and pseudoephedrines) and some of their derivatives have been broadly used as chiral ligands in catalysis or chiral inductors in asymmetric synthesis. Objective: This review focuses on recent progress in the use of ephedra compounds and their N-substituted derivatives as chiral auxiliaries in the area of asymmetric synthesis, via the alkylation reaction of the enolates derived from their corresponding N-Acyl or O-Acyl derivatives, in the C-C bond formation. Conclusion: A vast amount of work has been done about the use of ephedra compounds in asymmetric synthesis area, in general, it was found that pseudoephedrines are much more effective than ephedrines and are preferred as chiral auxiliaries in the asymmetric alkylation of the corresponding N-acyl amides or O-Acyl esters. Alkylation with alkyl halides requires the use of more than 4 equivalents of LiCl to accelerate the alkylation rate and to complete the reaction without effecting the diastereoselectivity of the process. In contrast, the use of secondary alkyl halides was found to make the reaction very slow. Furthermore, a lot of work about the alkylation reaction in the opening of epoxides and aziridines, aldolic condensation, Manich reaction, addition of nucleophiles to α,β-unsaturated ephedrine amides and Michael additions have been demonstrated to be effective in the C-C bond formation. The aldol reaction of chiral enolates, proceeds with decreasing yields and enantioselectivities as the steric demand of the α-R of ephedrine amides and the size of carbonyl compound increase. In addition, the use of branched groups on N,N-disubstituted norephedrine esters is highly recommended in the aldol reactions of aromatic and aliphatic aldehydes.In the case of N-Acyl or O-Acyl ephedrines supported on polymers, the reaction proceed with good enantioselectivities but low yields, the enantioselectivities are goods but the yields are low. In general, the removal step of the auxiliary proceeds with low to high yields but without epimerization.

ChemInform Abstract: Designing Chiral Quaternary Ammonium Polymers: Novel Type of Polymeric Catalyst for Asymmetric Alkylation Reaction.

ChemInform ◽  
2010 ◽  
Vol 41 (29) ◽  
pp. no-no
Author(s):  
Shinichi Itsuno ◽  
Devproshad K. Paul ◽  
Mikiya Ishimoto ◽  
Naoki Haraguchi
Keyword(s):  
Quaternary Ammonium ◽  
Alkylation Reaction ◽  
Asymmetric Alkylation ◽  
Polymeric Catalyst

ChemInform Abstract: Asymmetric Alkylation Reaction of α-Fluorotetralone under Phase-Transfer Catalyzed Conditions.

ChemInform ◽  
2010 ◽  
Vol 30 (47) ◽  
pp. no-no
Author(s):  
Shigeru Arai ◽  
Makoto Oku ◽  
Toshimasa Ishida ◽  
Takayuki Shioiri
Keyword(s):  
Phase Transfer ◽  
Alkylation Reaction ◽  
Asymmetric Alkylation

Designing Chiral Quaternary Ammonium Polymers: Novel Type of Polymeric Catalyst for Asymmetric Alkylation Reaction

2010 ◽  
Vol 39 (2) ◽  
pp. 86-87 ◽  
Author(s):  
Shinichi Itsuno ◽  
Devproshad K. Paul ◽  
Mikiya Ishimoto ◽  
Naoki Haraguchi
Keyword(s):  
Quaternary Ammonium ◽  
Alkylation Reaction ◽  
Asymmetric Alkylation ◽  
Polymeric Catalyst

scholarly journals Synthesis of 1,2,3-Triazolium Ionic Liquid-Supported Chiral Imidazolidinones and Their Application in Asymmetric Alkylation Reaction

Molecules ◽  
2019 ◽  
Vol 24 (18) ◽  
pp. 3349 ◽  
Author(s):  
Yunkyung Jeong ◽  
Yunjeong Park ◽  
Jae-Sang Ryu
Keyword(s):  
Ionic Liquid ◽  
Alkylation Reaction ◽  
Chiral Auxiliaries ◽  
Asymmetric Alkylation ◽  
Simple Extraction ◽  
Cleavage Reactions ◽  
Excellent Chemical

New 1,2,3-triazolium ionic liquid-supported chiral imidazolidinones were developed. The feasibility of the ionic liquid-supported imidazolidinones as chiral auxiliaries was demonstrated in sequential propionylation-alkylation-cleavage reactions, which provided the chiral product with good to excellent chemical yields (up to 90%) and high selectivities (up to 94% ee). The progress of the reactions could be monitored by TLC and NMR, and the ionic liquid-supported chiral auxiliaries could be recovered by simple extraction.

Asymmetric alkylation reaction of α-fluorotetralone under phase-transfer catalyzed conditions

1999 ◽  
Vol 40 (37) ◽  
pp. 6785-6789 ◽  
Author(s):  
Shigeru Arai ◽  
Makoto Oku ◽  
Toshimasa Ishida ◽  
Takayuki Shioiri
Keyword(s):  
Phase Transfer ◽  
Alkylation Reaction ◽  
Asymmetric Alkylation
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