scholarly journals Asymmetric Ring-Opening of Epoxides Catalyzed by Metal–Salen Complexes

Catalysts ◽  
2020 ◽  
Vol 10 (6) ◽  
pp. 705
Author(s):  
Anna Lidskog ◽  
Yutang Li ◽  
Kenneth Wärnmark
Keyword(s):  
Functional Groups ◽  
Organic Synthesis ◽  
Ring Opening ◽  
Kinetic Resolution ◽  
Catalytic Systems ◽  
Salen Complexes ◽  
Epoxide Opening ◽  
Ring Opening Of Epoxides ◽  
One Step ◽  
Asymmetric Ring Opening

The asymmetric ring-opening of epoxides is an important reaction in organic synthesis, since it allows for the enantioselective installation of two vicinal functional groups with specific stereochemistry within one step from a highly available starting material. An effective class of catalysts for the asymmetric ring-opening of epoxides is metal–salen complexes. This review summarizes the development of metal–salen catalyzed enantioselective desymmetrization of meso-epoxides and kinetic resolution of epoxides with various nucleophiles, including the design and application of both homogeneous- and heterogeneous epoxide-opening catalysts as well as multi-metallic covalent and supramolecular catalytic systems.

Electrophilic Ring Opening of Small Heterocycles

Synthesis ◽  
2017 ◽  
Vol 49 (24) ◽  
pp. 5307-5319 ◽  
Author(s):  
Chuan Wang
Keyword(s):  
Ethylene Oxide ◽  
Functional Groups ◽  
Organic Synthesis ◽  
Ring Opening ◽  
Building Blocks ◽  
Nickel Titanium ◽  
Ring Opening Reactions ◽  
Palladium Catalyzed ◽  
Ring Opening Of Epoxides ◽  
Nucleophilic Ring Opening

Small heterocycles, such as epoxides, aziridines, and ox­etanes are among the most useful building blocks in organic synthesis. Through electrophilic ring opening of these molecules, various electrophilic functional groups can be installed, which cannot be achieved via classic nucleophilic ring-opening reactions. In this review, the developments of electrophilic ring opening of small heterocycles are surveyed and organized according to the types of metal promoters.1 Introduction2 Electrophilic Ring Opening of Small Heterocycles Using Stoichiometric Metals2.1 Lithium-Mediated Electrophilic Ring Opening of Epoxides and Oxetanes2.2 Chromium-Mediated Electrophilic Ring Opening of Vinyl Epoxides2.3 Tin-Mediated Electrophilic Ring Opening of Vinyl Epoxides2.4 Samarium-Mediated Electrophilic Ring Opening of Vinyl and Alkynyl Epoxides2.5 Titanium-Mediated Electrophilic Ring Opening of Epoxides2.6 Platinum, Palladium, and Nickel-Mediated Electrophilic Ring Opening of 1,1-Dimethyl Ethylene Oxide3 Catalytic Electrophilic Ring Opening of Small Heterocycles3.1 Titanium-Catalyzed Electrophilic Ring Opening of Epoxides3.2 Palladium-Catalyzed Electrophilic Ring Opening of Vinyl and Alkynyl Small Heterocycles3.3 Iron-Catalyzed Electrophilic Ring Opening of Oxetanes3.4 Scandium-Catalyzed Electrophilic Ring Opening of Vinyl Epoxides3.5 Iridium-Catalyzed Electrophilic Ring Opening of 2-Methyl 2-Vinyl­oxiranes3.6 Nickel-Catalyzed Electrophilic Ring Opening of Epoxides and Aziridines3.7 Nickel–Titanium-Cocatalyzed Electrophilic Ring Opening of Epoxides4 Summary

Dinuclear salen cobalt complex incorporating Y(OTf)3: enhanced enantioselectivity in the hydrolytic kinetic resolution of epoxides

RSC Advances ◽  
2015 ◽  
Vol 5 (101) ◽  
pp. 82699-82703 ◽  
Author(s):  
Deepak Patel ◽  
Ganesh Ram Kurrey ◽  
Sandip S. Shinde ◽  
Pradeep Kumar ◽  
Geon-Joong Kim ◽  
...  
Keyword(s):  
Electron Transfer ◽  
Ring Opening ◽  
Kinetic Resolution ◽  
Cobalt Complex ◽  
Promoting Effect ◽  
Hydrolytic Kinetic Resolution ◽  
Ring Opening Of Epoxides ◽  
Asymmetric Ring Opening

Yttrium triflate present in dinuclear salen cobalt complex not only shows a promoting effect on electron transfer, but also assists in the asymmetric ring opening of epoxides with water efficiently.

Catalytic Asymmetric Transformations of Racemic Aziridines

Synthesis ◽  
2020 ◽  
Vol 52 (12) ◽  
pp. 1738-1750 ◽  
Author(s):  
Zhuo Chai
Keyword(s):  
Ring Opening ◽  
Kinetic Resolution ◽  
Short Review ◽  
Asymmetric Transformations ◽  
Parallel Kinetic Resolution ◽  
Donor Acceptor ◽  
Molecular Architectures ◽  
Catalytic Asymmetric ◽  
Asymmetric Transformation ◽  
Asymmetric Ring Opening

The catalytic asymmetric ring-opening transformations of aziridines represent an important strategy for the construction of various chiral nitrogen-containing molecular architectures. This short review covers the progress achieved in the catalytic asymmetric transformation of racemic aziridines, focusing on the catalytic strategies employed for each different type of such aziridines.1 Introduction2 Reaction of Racemic 2-Vinylaziridines3 Reaction of Racemic 2-Alkylaziridines3.1 Regiodivergent Parallel Kinetic Resolution3.2 Kinetic Resolution4 Reaction of Racemic 2-(Hetero)arylaziridines4.1 Kinetic Resolution4.2 Enantioconvergent Transformation5 Reaction of Racemic Donor–Acceptor-Type Aziridines6 Conclusion and Outlook

Chiral (Salen) Complexes Encapsulated in Mesoporous ZSM-5 as an Optical Active Catalyst for Asymmetric Phenolic Ring Opening of Terminal Epoxides

2007 ◽  
Vol 124-126 ◽  
pp. 1809-1812
Author(s):  
Kwang Yeon Lee ◽  
Young Hee Lee ◽  
Chang Kyo Shin ◽  
Geon Joong Kim
Keyword(s):  
Ring Opening ◽  
Acidic Solution ◽  
Active Catalyst ◽  
Immobilized Catalysts ◽  
Phenolic Ring ◽  
Salen Complexes ◽  
Ring Opening Of Epoxides ◽  
Very High ◽  
Chiral Salen Complexes

ZSM-5 was modified by alkaline and acidic solution to introduce mesoporosity in the crystals. Heterogenized Co(III) salen was prepared in the mesopores of ZSM-5 by ‘ship-in-a-bottle’ method. Phenolic ring opening of epoxides was performed successfully by using encapsulated chiral salen catalysts. Very high enantioselectivity and conversion were obtained in PKR reaction by immobilized catalysts.

Asymmetric ring opening of epoxides with cyanides catalysed by chiral binuclear titanium complexes

2014 ◽  
Vol 25 (10-11) ◽  
pp. 838-843 ◽  
Author(s):  
Victor I. Maleev ◽  
Denis A. Chusov ◽  
Lidiya V. Yashkina ◽  
Nikolai S. Ikonnikov ◽  
Michail M. Il’in
Keyword(s):  
Ring Opening ◽  
Titanium Complexes ◽  
Ring Opening Of Epoxides ◽  
Asymmetric Ring Opening

scholarly journals Cobalt Catalysis Enables Regioselective Ring-opening of Epoxides with Aryl Halides

2021 ◽  
Author(s):  
Aleksandra Potrząsaj ◽  
Mateusz Musiejuk ◽  
Wojciech Chaładaj ◽  
Maciej Giedyk ◽  
Dorota Gryko
Keyword(s):  
Vitamin B12 ◽  
Organic Synthesis ◽  
Blue Light ◽  
Catalytic System ◽  
Ring Opening ◽  
Aryl Halides ◽  
Light Irradiation ◽  
Selective Synthesis ◽  
Ring Opening Of Epoxides

Ring-opening of epoxides furnishing either linear or branched products belongs to the group of classic transformations in organic synthesis. However, the regioselective cross-electrophile coupling of aryl epoxides with aryl halides still represents a key challenge. Herein, we report vitamin B12/Ni dual-catalytic system that allows for the selective synthesis of linear products under blue-light irradiation.

Asymmetric Ring Opening of Epoxides

ChemInform ◽  
2005 ◽  
Vol 36 (24) ◽  
Author(s):  
I. M. Pastor ◽  
M. Yus
Keyword(s):  
Ring Opening ◽  
Ring Opening Of Epoxides ◽  
Asymmetric Ring Opening
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