scholarly journals Synthetic and biosynthetic methods for selective cyclisations of 4,5-epoxy alcohols to tetrahydropyrans

2022 ◽  
Author(s):  
James I. Bowen ◽  
Luoyi Wang ◽  
Matthew P. Crump ◽  
Christine L. Willis
Keyword(s):  
Natural Products ◽  
Ring Opening ◽  
Epoxide Ring ◽  
Biosynthetic Pathways ◽  
Epoxide Ring Opening ◽  
Epoxy Alcohols

In this review, methods for the selective intramolecular epoxide ring opening (IERO) of 4,5-epoxy-alcohols are discussed as well as biosynthetic pathways to tetrahydropyran-containing natural products which utilise IERO reactions.

ChemInform Abstract: NEIGHBORING GROUP EFFECTS IN EPOXIDE RING OPENING, CIS-EPOXY-ALCOHOLS

1976 ◽  
Vol 7 (42) ◽  
pp. no-no
Author(s):  
ERWIN GLOTTER ◽  
PNINA KRINSKY ◽  
MIRIAM REJTOE ◽  
MARTIN WEISSENBERG
Keyword(s):  
Ring Opening ◽  
Epoxide Ring ◽  
Neighboring Group ◽  
Epoxide Ring Opening ◽  
Epoxy Alcohols ◽  
Group Effects

Active Copper Catalyzed Regioselective Ring Opening of Epoxides by Heterocyclic Amines: An Efficient Protocol for Synthesis of β-Amino Alcohols

2019 ◽  
Vol 4 (3) ◽  
pp. 194-199
Author(s):  
Santosh S. Devkate ◽  
Arvind S. Burungale ◽  
Ashok S. Pise ◽  
Sunil D. Jadhav
Keyword(s):  
Natural Products ◽  
Carbon Atom ◽  
Ring Opening ◽  
Amino Alcohols ◽  
Heterocyclic Amines ◽  
Epoxide Ring ◽  
Epoxide Ring Opening ◽  
Ring Opening Of Epoxide ◽  
Ring Opening Of Epoxides

The regioselective epoxide ring opening at less substituted carbon atom of epoxide were reported by nucleophiles like heterocyclic amines which gives well known 1,2-difunctionalized amino alcohols. These are present in many synthetic as well as natural products. The ring opening of epoxide is achieved by cleavage with amines in presence of copper(0) as a catalyst. It is observed that the lithium napthalenide reduction of copper(I) produces a highly reactive form of copper(0) that acts as a catalyst for ring opening of epoxides with an amine.

Neighbouring group effects in epoxide ring opening; cis-epoxy-alcohols

1976 ◽  
pp. 1442-1445 ◽  
Author(s):  
Erwin Glotter ◽  
Pnina Krinsky ◽  
Miriam Rejtö ◽  
Martin Weissenberg
Keyword(s):  
Ring Opening ◽  
Epoxide Ring ◽  
Epoxide Ring Opening ◽  
Epoxy Alcohols ◽  
Group Effects

scholarly journals 1-Tosyl-6-vinyl-4,5,6,7-tetrahydro-1H-benzo [d] imidazole-2-amine

Molbank ◽  
10.3390/m1262 ◽  
2021 ◽  
Vol 2021 (3) ◽  
pp. M1262
Author(s):  
Fiach B. Meany ◽  
Sarah O’Rourke ◽  
Paul V. Murphy
Keyword(s):  
Natural Products ◽  
Nmr Spectroscopy ◽  
1H Nmr ◽  
13C Nmr ◽  
Title Compound ◽  
Ring Opening ◽  
13C Nmr Spectroscopy ◽  
Amino Alcohols ◽  
Epoxide Ring ◽  
Epoxide Ring Opening

The alkene functionalised 2-aminobenzimidazole ring found in terrazoanthine natural products was synthesized in 3 steps from 1,2-epoxy-4-vinylcyclohexane via epoxide ring opening with toluenesulphonamide yielding 2 regioisomeric, separable amino alcohols. One isomer was oxidized to the corresponding ketone and subsequently condensed with cyanamide to furnish the title compound, which was characterized by 1H-NMR and 13C-NMR spectroscopy.

Bimetallic Radical Redox-Relay Catalysis for the Isomerization of Epoxides to Allylic Alcohols

2019 ◽  
Author(s):  
Ke-Yin Ye ◽  
Terry McCallum ◽  
Song Lin
Keyword(s):  
Ring Opening ◽  
High Reactivity ◽  
Hydrogen Atom Transfer ◽  
Organic Radicals ◽  
Epoxide Ring ◽  
Allylic Alcohols ◽  
Epoxide Ring Opening ◽  
Bond Forming ◽  
Co Catalysts ◽  
The Rich

Organic radicals are generally short-lived intermediates with exceptionally high reactivity. Strategically, achieving synthetically useful transformations mediated by organic radicals requires both efficient initiation and selective termination events. Here, we report a new catalytic strategy, namely bimetallic radical redox-relay, in the regio- and stereoselective rearrangement of epoxides to allylic alcohols. This approach exploits the rich redox chemistry of Ti and Co complexes and merges reductive epoxide ring opening (initiation) with hydrogen atom transfer (termination). Critically, upon effecting key bond-forming and -breaking events, Ti and Co catalysts undergo proton-transfer/electron-transfer with one another to achieve turnover, thus constituting a truly synergistic dual catalytic system.<br>

Construction the A-B bicyclic ring structure of Stemocurtisisne

2020 ◽  
Vol 17 ◽  
Author(s):  
Duc Dau Xuan
Keyword(s):  
Glutamic Acid ◽  
Natural Product ◽  
Mannich Reaction ◽  
Boronic Acid ◽  
Ring Opening ◽  
Ring Structure ◽  
Starting Material ◽  
Epoxide Ring ◽  
Epoxide Ring Opening

: The synthesis of the A-B bicyclic ring structure 3 of the natural product Stemocurtisine is described. The synthesis was accomplished in seven synthetic steps from commercially available L-glutamic acid. The key step involved a borono-Mannich reaction between the hemiaminal 6 and trans-β-styryl boronic acid and trans-β-styrylpotassiumtrifluoroborate to prepare the cis diene 4. Attempts to prepare the A-B-C ring compound 2 via intramolecular epoxide ring opening followed by rearangement under different basic conditions were unsuccessful. Only unreactive starting material was recovered.

The epoxide ring opening of 2-O-acyl-1,6:3,4-dianhydro-β-D-galactopyranoses

1971 ◽  
Vol 36 (4) ◽  
pp. 1487-1495 ◽  
Author(s):  
M. Prystaš ◽  
H. Gustafsson ◽  
F. Šorm
Keyword(s):  
Ring Opening ◽  
Epoxide Ring ◽  
Epoxide Ring Opening

scholarly journals Thermal and Electrochemical Properties of Solid Polymer Electrolytes Prepared via Lithium Salt-Catalyzed Epoxide Ring Opening Polymerization

2021 ◽  
Vol 11 (4) ◽  
pp. 1561
Author(s):  
Gabrielle Foran ◽  
Nina Verdier ◽  
David Lepage ◽  
Arnaud Prébé ◽  
David Aymé-Perrot ◽  
...  
Keyword(s):  
Electrochemical Properties ◽  
Polymer Electrolytes ◽  
Ring Opening ◽  
Lithium Salt ◽  
Ring Opening Polymerization ◽  
Solid Polymer Electrolytes ◽  
Solid Polymer ◽  
Polymerization Reaction ◽  
Epoxide Ring ◽  
Epoxide Ring Opening

Solid polymer electrolytes have been widely proposed for use in all solid-state lithium batteries. Advantages of polymer electrolytes over liquid and ceramic electrolytes include their flexibility, tunability and easy processability. An additional benefit of using some types of polymers for electrolytes is that they can be processed without the use of solvents. An example of polymers that are compatible with solvent-free processing is epoxide-containing precursors that can form films via the lithium salt-catalyzed epoxide ring opening polymerization reaction. Many polymers with epoxide functional groups are liquid under ambient conditions and can be used to directly dissolve lithium salts, allowing the reaction to be performed in a single reaction vessel under mild conditions. The existence of a variety of epoxide-containing polymers opens the possibility for significant customization of the resultant films. This review discusses several varieties of epoxide-based polymer electrolytes (polyethylene, silicone-based, amine and plasticizer-containing) and to compare them based on their thermal and electrochemical properties.

An analysis of the factors contributing to the regioselectivity observed in the opening of oxiranes

1980 ◽  
Vol 58 (3) ◽  
pp. 302-306 ◽  
Author(s):  
Margaret M. Kayser ◽  
Peter Morand
Keyword(s):  
Oxygen Atom ◽  
Ring Opening ◽  
Oxirane Ring ◽  
Epoxide Ring ◽  
Acid Base ◽  
Epoxide Ring Opening ◽  
Soft Acid ◽  
Hsab Theory

The regioselectivity of epoxide ring opening can be analyzed in terms of hard–soft acid–base (HSAB) theory. The coordination of the hard acid with the oxygen atom of the oxirane ring produces a "pulling effect" which determines the direction of the ring opening. In the absence of a strong "pulling effect" the "pushing effect" of the approaching base is examined and the consequences of relative softness or hardness of the nucleophile on the regioselectivity of the ring opening are discussed.

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