Aza-Michael Addition of Imidazoles to α,β-Unsaturated Compounds and Synthesis of β-Amino Alcohols via Nucleophilic Ring Opening of Epoxides Using Copper(II) Acetylacetonate (Cu(acac)2) Immobilized in Ionic Liquids

2007 ◽  
Vol 46 (25) ◽  
pp. 8614-8619 ◽  
Author(s):  
M. Lakshmi Kantam ◽  
B. Neelima ◽  
Ch. Venkat Reddy ◽  
Rajashree Chakravarti
Keyword(s):  
Ionic Liquids ◽  
Michael Addition ◽  
Ring Opening ◽  
Amino Alcohols ◽  
Unsaturated Compounds ◽  
Ring Opening Of Epoxides ◽  
Nucleophilic Ring Opening

An efficient method for regioselective ring opening of epoxides by amines under microwave irradiation using Bi(NO3)3·5H2O as a catalyst

2017 ◽  
Vol 41 (7) ◽  
pp. 2668-2671 ◽  
Author(s):  
Shobha Bansal ◽  
Yogendra Kumar ◽  
Parveen Pippal ◽  
Dipak K. Das ◽  
Panchanan Pramanik ◽  
...  
Keyword(s):  
Microwave Irradiation ◽  
Efficient Method ◽  
Ring Opening ◽  
Amino Alcohols ◽  
Solvent Free ◽  
Environmentally Benign ◽  
Highly Efficient ◽  
Ring Opening Of Epoxides ◽  
Nucleophilic Ring Opening

Bi(NO3)3·5H2O a highly efficient environmentally benign catalyst, is used for the nucleophilic ring opening of epoxides with aromatic, aliphatic and heteroaromatic amines under solvent free microwave conditions to afford the corresponding β-amino alcohols in good to excellent yields with high regioselectivity.

Indium(I) iodide promoted cleavage of dialkyl disulfides — Application of the Michael addition of thiolate anions to conjugated carbonyl compounds and regioselective ring opening of epoxides

2006 ◽  
Vol 84 (5) ◽  
pp. 762-770 ◽  
Author(s):  
Brindaban C Ranu ◽  
Tanmay Mandal
Keyword(s):  
Michael Addition ◽  
Ring Opening ◽  
Unsaturated Ketones ◽  
Ring Opening Of Epoxides ◽  
Dialkyl Disulfides ◽  
Carboxylic Esters ◽  
Thiolate Anions ◽  
Neutral Conditions ◽  
Nucleophilic Ring Opening ◽  
The Michael Addition

Indium(I) iodide promotes cleavage of dialkyl disulfides generating thiolate anions that then undergo facile addition to α,β-unsaturated ketones, aldehydes, carboxylic esters, and nitriles under neutral conditions producing corresponding β-ketosulfides or β-cyanosulfides. This strategy has also been used for the regioselective nucleophilic ring opening of epoxides by thiolate anions in presence of indium(III) chloride producing corresponding β-hydroxyphenyl sulfides. The reactions are in general, very clean, high yielding, and reasonably fast. Thus, simple and convenient procedures for the synthesis of β-ketosulfides or β-cyanosulfides and β-hydroxyalkyl sulfides have been developed using this cleavage reaction.Key words: indium(I) iodide, Michael addition, β-ketosulfide, β-cyanosulfide, epoxide, β-hydroxy sulfide.

Nucleophilic ring opening of trans-2,3-disubstituted epoxides to β-amino alcohols with catalyst-controlled regioselectivity

2018 ◽  
Vol 54 (92) ◽  
pp. 12998-13001 ◽  
Author(s):  
Michelle Lee ◽  
Jessica R. Lamb ◽  
Maria J. Sanford ◽  
Anne M. LaPointe ◽  
Geoffrey W. Coates
Keyword(s):  
Ring Opening ◽  
Amino Alcohols ◽  
Nucleophilic Ring Opening

We report the nucleophilic ring opening of unsymmetrical trans-epoxides to β-amino alcohols with catalyst-controlled regioselectivity.

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.

Highly regioselective ring-opening of epoxides with amines: a metal- and solvent-free protocol for the synthesis of β-amino alcohols

2020 ◽  
Vol 56 (15) ◽  
pp. 2256-2259
Author(s):  
Dong Li ◽  
Jing Wang ◽  
Shibo Yu ◽  
Silei Ye ◽  
Wenjie Zou ◽  
...  
Keyword(s):  
Acetic Acid ◽  
Ring Opening ◽  
Amino Alcohols ◽  
Solvent Free ◽  
Ring Opening Reaction ◽  
Ring Opening Of Epoxides

We herein report a metal- and solvent-free acetic acid-mediated ring-opening reaction of epoxides with amines.

Synthesis of β-amino alcohols using MgO as a new catalyst under solvent-free conditions

2008 ◽  
Vol 86 (1) ◽  
pp. 65-71 ◽  
Author(s):  
Mona Hosseini-Sarvari
Keyword(s):  
Ring Opening ◽  
Amino Alcohols ◽  
Solvent Free ◽  
Aliphatic Amines ◽  
Solvent Free Conditions ◽  
Ring Opening Of Epoxides ◽  
High Yields ◽  
Aromatic And Aliphatic Amines

MgO catalyzed efficiently the ring opening of epoxides with a range of aromatic and aliphatic amines to produce β-substituted alcohols in high yields under solvent-free conditions. Exclusive trans stereoselectivity is observed for cyclic epoxide.Key words: MgO, β-amino alcohols, solvent-free, epoxide, amine.

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.

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