An improved procedure to prepare 3-methyl-4-nitroalkylenethylisoxazoles and their reaction under catalytic enantioselective Michael addition with nitromethane-Reference-Cited by-同舟云学术

An improved procedure to prepare 3-methyl-4-nitroalkylenethylisoxazoles and their reaction under catalytic enantioselective Michael addition with nitromethane

Published:2015 Issue:7 Volume:13 Page:2192-2195
ISSN:1477-0520
Container-title:Organic & Biomolecular Chemistry
language:en
Short-container-title:Org. Biomol. Chem.

Author:

Moccia Maria¹²³⁴⁵,Wells Robert J.¹²³⁴⁵,Adamo Mauro. F. A.¹²³⁴⁵

Affiliation:

1. Centre for Synthesis and Chemical Biology (CSCB)

2. Department of Pharmaceutical and Medicinal Chemistry

3. Royal College of Surgeons in Ireland

4. Dublin 2

5. Ireland

Abstract

A two-step preparation of 3-methyl-4-nitro-5-alkylethenyl isoxazoles is herein reported. These were reacted with nitromethane under phase-transfer catalysis to provide highly enantioenriched adducts (up to 93% ee).

Publisher

Royal Society of Chemistry (RSC)

Subject

Organic Chemistry,Physical and Theoretical Chemistry,Biochemistry

Link

http://pubs.rsc.org/en/content/articlepdf/2015/OB/C4OB02109F

Reference22 articles.

1. Quality by design (QbD) of amide isosteres: 5,5-Disubstituted isoxazolines as potent CRTh2 antagonists with favorable pharmacokinetic and drug-like properties

2. A Mild and Chemoselective Method for the Reduction of Conjugated Isoxazolines to β-Hydroxy Ketones

3. New Perspectives in Oxazole Chemistry. 2.1 One-Pot Efficient Access to Polyfunctionalized Nitroenamines by Nucleophilic Ring Opening of 4-Nitro Derivatives

4. New Perspectives in Oxazole Chemistry: Synthesis and Cycloaddition Reactions of a 4-Nitro-2-phenyl Derivative1

Cited by 35 articles. 订阅此论文施引文献订阅此论文施引文献，注册后可以免费订阅5篇论文的施引文献，订阅后可以查看论文全部施引文献

1. 5‐Styrylisoxazoles: π‐Conjugated System with Fluorescent Properties and Bioactivity;ChemistrySelect;2023-05-24

2. Asymmetric Phase Transfer Catalysed Michael Addition of γ-Butenolide and N-Boc-Pyrrolidone to 4-Nitro-5-styrylisoxazoles;Catalysts;2022-06-10

3. Organic Transformations with MeNO ₂;The Chemical Transformations of C1 Compounds;2022-01-21

4. Recent development in asymmetric organocatalytic domino reactions involving 1,6-addition as a key step;Organic Chemistry Frontiers;2022

5. Natural and Synthetic Halogenated Amino Acids—Structural and Bioactive Features in Antimicrobial Peptides and Peptidomimetics;Molecules;2021-12-06