Aluminium triflate: a remarkable Lewis acid catalyst for the ring opening of epoxides by alcohols

2005 ◽  
Vol 3 (18) ◽  
pp. 3269 ◽  
Author(s):  
D. Bradley G. Williams ◽  
Michelle Lawton
Keyword(s):  
Lewis Acid ◽  
Ring Opening ◽  
Acid Catalyst ◽  
Ring Opening Of Epoxides ◽  
Lewis Acid Catalyst

scholarly journals Anhydrous Titanium(III) chloride as a New Lewis-Acid Catalyst for Ring Opening of Epoxides with Aromatic Amines

2007 ◽  
Vol 2 (2) ◽  
pp. 1934578X0700200
Author(s):  
Suchitra Bhatt ◽  
Sandip K. Nayak
Keyword(s):  
Ambient Temperature ◽  
Lewis Acid ◽  
Aromatic Amines ◽  
Ring Opening ◽  
Acid Catalyst ◽  
Amino Alcohols ◽  
Azide Ion ◽  
Ring Opening Of Epoxides ◽  
Lewis Acid Catalyst

Anhydrous titanium(III) chloride was found to be a simple and efficient Lewis acid catalyst for ring opening of epoxides at ambient temperature. The reaction proceeded smoothly with anilines as well as azide ion as nucleophiles to give the corresponding β-amino alcohols and β-azido alcohols in moderate to good yields.

scholarly journals Catalytic, Transannular Carbonyl-Olefin Metathesis Reactions

2019 ◽  
Author(s):  
Paul Riehl ◽  
Daniel Nasrallah ◽  
Corinna Schindler
Keyword(s):  
Lewis Acid ◽  
Olefin Metathesis ◽  
Ring Opening ◽  
Acid Catalyst ◽  
Catalyst Design ◽  
Lewis Acid Catalysts ◽  
Complex Molecules ◽  
New Class ◽  
Metathesis Reactions ◽  
Lewis Acid Catalyst

A new class of Lewis acid-catalyzed carbonyl-olefin metathesis reactions is described that complements existing protocols for related ring-closing, ring-opening, and intermolecular transformations. These transannular carbonyl-olefin metathesis reactions rely on FeCl<sub>3</sub> as an inexpensive Lewis acid catalyst and are mechanistically distinct from previously developed protocols for ring closing, ring-opening and intermolecular metathesis. Specifically, carbonyl-ene and carbonyl-olefin metathesis reaction paths are competing to ultimately favor metathesis as the thermodynamic product. Importantly, we show that distinct Lewis acid catalysts are able to differentiate between these pathways to enable the selective formation of transannular carbonyl-ene or carbonyl-olefin metathesis products thus providing a valuable approach to the molecular editing of naturally occurring complex molecules. Additionally, these results are expected to enable further advances in catalyst design for carbonyl-olefin metathesis to ultimately develop efficient and high-yielding catalytic carbonyl olefination reactions.

scholarly journals Catalytic, Transannular Carbonyl-Olefin Metathesis Reactions

2019 ◽  
Author(s):  
Paul Riehl ◽  
Daniel Nasrallah ◽  
Corinna Schindler
Keyword(s):  
Lewis Acid ◽  
Olefin Metathesis ◽  
Ring Opening ◽  
Acid Catalyst ◽  
Catalyst Design ◽  
Lewis Acid Catalysts ◽  
Complex Molecules ◽  
New Class ◽  
Metathesis Reactions ◽  
Lewis Acid Catalyst

A new class of Lewis acid-catalyzed carbonyl-olefin metathesis reactions is described that complements existing protocols for related ring-closing, ring-opening, and intermolecular transformations. These transannular carbonyl-olefin metathesis reactions rely on FeCl<sub>3</sub> as an inexpensive Lewis acid catalyst and are mechanistically distinct from previously developed protocols for ring closing, ring-opening and intermolecular metathesis. Specifically, carbonyl-ene and carbonyl-olefin metathesis reaction paths are competing to ultimately favor metathesis as the thermodynamic product. Importantly, we show that distinct Lewis acid catalysts are able to differentiate between these pathways to enable the selective formation of transannular carbonyl-ene or carbonyl-olefin metathesis products thus providing a valuable approach to the molecular editing of naturally occurring complex molecules. Additionally, these results are expected to enable further advances in catalyst design for carbonyl-olefin metathesis to ultimately develop efficient and high-yielding catalytic carbonyl olefination reactions.

scholarly journals Catalytic, Transannular Carbonyl-Olefin Metathesis Reactions

2019 ◽  
Author(s):  
Paul Riehl ◽  
Daniel Nasrallah ◽  
Corinna Schindler
Keyword(s):  
Lewis Acid ◽  
Olefin Metathesis ◽  
Ring Opening ◽  
Acid Catalyst ◽  
Catalyst Design ◽  
Lewis Acid Catalysts ◽  
Complex Molecules ◽  
New Class ◽  
Metathesis Reactions ◽  
Lewis Acid Catalyst

A new class of Lewis acid-catalyzed carbonyl-olefin metathesis reactions is described that complements existing protocols for related ring-closing, ring-opening, and intermolecular transformations. These transannular carbonyl-olefin metathesis reactions rely on FeCl<sub>3</sub> as an inexpensive Lewis acid catalyst and are mechanistically distinct from previously developed protocols for ring closing, ring-opening and intermolecular metathesis. Specifically, carbonyl-ene and carbonyl-olefin metathesis reaction paths are competing to ultimately favor metathesis as the thermodynamic product. Importantly, we show that distinct Lewis acid catalysts are able to differentiate between these pathways to enable the selective formation of transannular carbonyl-ene or carbonyl-olefin metathesis products thus providing a valuable approach to the molecular editing of naturally occurring complex molecules. Additionally, these results are expected to enable further advances in catalyst design for carbonyl-olefin metathesis to ultimately develop efficient and high-yielding catalytic carbonyl olefination reactions.

Mesoporous Zr-Beta zeolites prepared by a post-synthetic strategy as a robust Lewis acid catalyst for the ring-opening aminolysis of epoxides

2015 ◽  
Vol 17 (3) ◽  
pp. 1744-1755 ◽  
Author(s):  
Bo Tang ◽  
Weili Dai ◽  
Xiaoming Sun ◽  
Guangjun Wu ◽  
Naijia Guan ◽  
...  
Keyword(s):  
Mass Transfer ◽  
Catalytic Activity ◽  
Lewis Acid ◽  
Ring Opening ◽  
Acid Catalyst ◽  
Amino Alcohols ◽  
Synthetic Strategy ◽  
Beta Zeolites ◽  
Lewis Acid Catalyst ◽  
Catalytic Deactivation

Mesoporous Zr-Beta exhibits a remarkable catalytic activity and regio-selectivity to β-amino alcohols in epoxide aminolysis. Intra-crystalline mesopores greatly promote the reaction through enhanced mass transfer and suppress the catalytic deactivation.

Epoxide ring opening in a zinc(II) complex in water without any Lewis acid catalyst: Formation of only one diastereomer out of 23

2011 ◽  
Vol 375 (1) ◽  
pp. 101-105 ◽  
Author(s):  
Nirmal K. Shee ◽  
F.A. Oluwafunmilayo Adekunle ◽  
Debashree Das ◽  
Michael G.B. Drew ◽  
Dipankar Datta
Keyword(s):  
Lewis Acid ◽  
Ring Opening ◽  
Acid Catalyst ◽  
Epoxide Ring ◽  
Epoxide Ring Opening ◽  
Lewis Acid Catalyst ◽  
Catalyst Formation
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