4.8 Article

A Stereospecific Alkene 1,2-Aminofunctionalization Platform for the Assembly of Complex Nitrogen-Containing Ring Systems

Related references

Note: Only part of the references are listed.
Article Multidisciplinary Sciences

Asymmetric synthesis of N-bridged [3.3.1] ring systems by phosphonium salt/Lewis acid relay catalysis

Jian-Ping Tan et al.

Summary: This study presents a general method for constructing optically pure pseudo-natural products (PNPs) bearing N-bridged [3.3.1] ring systems through bifunctional phosphonium salt/Lewis acid relay catalysis. The method shows wide compatibility with various substrates and exhibits excellent reactivities and stereoselectivities. The obtained enantioenriched products demonstrate potential anticancer activities. This research opens up new opportunities for the catalytic synthesis of challenging chiral pseudo-natural products and offers prospects for bioactive small-molecule discovery.

NATURE COMMUNICATIONS (2022)

Review Chemistry, Organic

Transition Metal-Catalyzed Carboamination of Alkenes and Allenes: Recent Progress

Santosh Kumar Nanda et al.

Summary: Vicinal carboamination of carbon-carbon multiple bonds is a reliable and efficient strategy for the quick preparation of valuable amine derivatives. Transition metal catalysis has been employed for the synthesis of N-bearing entities through inter- and intramolecular carboamination of alkenes and allenes. However, literature on carboamination of allenes is lacking compared to that on alkenes.

ASIAN JOURNAL OF ORGANIC CHEMISTRY (2022)

Article Chemistry, Multidisciplinary

Synergistic Catalysis between a Dipeptide Phosphonium Salt and a Metal-Based Lewis Acid for Asymmetric Synthesis of N-Bridged [3.2.1] Ring Systems

Yuan Chen et al.

Summary: This paper presents an unprecedented synergic catalytic route for the asymmetric construction of fluorinated N-bridged [3.2.1] cyclic members of tropane family through a bifunctional phosphonium salt/silver co-catalyzed cyclization process. A wide range of substrates bearing various functional groups are compatible with this method, providing targeted compounds with seven-membered rings and four contiguous stereocenters in high yields and excellent stereoselectivities.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2022)

Article Chemistry, Medicinal

Spirocyclic Scaffolds in Medicinal Chemistry

Kerstin Hiesinger et al.

Summary: Spirocyclic scaffolds are widely used in drugs, and the interest in nonplanar bioactive compounds is growing. This article summarizes different synthetic routes to obtain spirocyclic systems, discussing their impact on potency and selectivity, as well as changes in physicochemical properties and ADME in vitro and in vivo.

JOURNAL OF MEDICINAL CHEMISTRY (2021)

Article Chemistry, Medicinal

Identification, semisynthesis, and anti-inflammatory evaluation of 2,3-seco-clavine-type ergot alkaloids from human intestinal fungus Aspergillus fumigatus CY018

Juan Zhang et al.

Summary: Intestinal commensal fungi produce 2,3-seco ergot alkaloids that are crucial for human health, with secofumigaclavine B (4) showing potential anti-inflammatory effects and being considered as a candidate for MD2 inhibitors development. These findings provide insight into the importance of intestinal fungi metabolites and their role in human health.

EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY (2021)

Review Chemistry, Organic

Catalytic, Enantioselective Diamination of Alkenes

Zhong-Lin Tao et al.

Summary: Enantioselective diamination of alkenes is an important method for accessing enantioenriched, vicinal diamines, with broad applications in asymmetric synthesis. Despite lagging behind dihydroxylation of olefins, successful methods using different reaction mechanisms have been developed for enantioselective olefin diamination. This review highlights recent advances and limitations in the field, aiming to inspire further developments.

SYNTHESIS-STUTTGART (2021)

Review Chemistry, Organic

Recent advances in aminative difunctionalization of alkenes

Ziying Wu et al.

Summary: This review outlines the major developments in transition metal-catalyzed or metal-free diamination, aminohalogenation, aminocarbonation, amino-oxidation, and aminoboronation reactions of alkenes from 2015-2020. It highlights the efficiency and advantages of the aminative difunctionalization of alkenes in synthesizing nitrogen-containing compounds, which are widely found in natural and synthetic products. The construction of C-N bonds from simple and easily available raw materials has been a topic of interest to chemists, especially in the synthesis of drugs.

ORGANIC & BIOMOLECULAR CHEMISTRY (2021)

Review Chemistry, Organic

Beyond osmium: progress in 1,2-amino oxygenation of alkenes, 1,3-dienes, alkynes, and allenes

Brett N. Hemric

Summary: 1,2-Amino oxygenation is an important synthetic strategy for the synthesis of pharmaceuticals, natural products, and synthetic ligands, with a wide range of applications. Modern chemistry has developed a variety of novel methods for 1,2-amino oxygenation, such as using different transition metals and electrochemical, photochemical, and biochemical reactions.

ORGANIC & BIOMOLECULAR CHEMISTRY (2021)

Article Chemistry, Organic

Intramolecular N-Me and N-H aminoetherification for the synthesis of N-unprotected 3-amino-O-heterocycles

Mahesh P. Paudyal et al.

Summary: A mild Rh-catalyzed method has been developed for the synthesis of cyclic unprotected N-Me and N-H 2,3-aminoethers using an olefin aziridination-aziridine ring-opening domino reaction. This method is effectively applicable to the stereocontrolled synthesis of a variety of 2,3-disubstituted aminoether O-heterocyclic scaffolds, including tetrahydrofurans, tetrahydropyrans and chromanes.

ORGANIC & BIOMOLECULAR CHEMISTRY (2021)

Article Chemistry, Multidisciplinary

Stereospecific Alkene Aziridination Using a Bifunctional Amino-Reagent: An Aza-Prilezhaev Reaction

Joshua J. Farndon et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2018)

Article Chemistry, Organic

Oxidative allene amination for the synthesis of nitrogen-containing heterocycles

Josephine Eshon et al.

ARKIVOC (2018)

Review Chemistry, Multidisciplinary

The Baldwin rules: revised and extended

Kerry Gilmore et al.

WILEY INTERDISCIPLINARY REVIEWS-COMPUTATIONAL MOLECULAR SCIENCE (2016)

Article Chemistry, Multidisciplinary

Vicinal Diamination of Alkenes under Rh-Catalysis

David E. Olson et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2014)

Article Chemistry, Organic

Methods for direct alkene diamination, new & old

Sam De Jong et al.

TETRAHEDRON (2012)

Article Chemistry, Medicinal

What Do Medicinal Chemists Actually Make? A 50-Year Retrospective

W. Patrick Walters et al.

JOURNAL OF MEDICINAL CHEMISTRY (2011)

Article Chemistry, Organic

Nitrenium Ion-Mediated Alkene Bis-Cyclofunctionalization: Total Synthesis of (-)-Swainsonine

Duncan J. Wardrop et al.

ORGANIC LETTERS (2011)

Article Chemistry, Multidisciplinary

Metal-Free Highly Regioselective Aminotrifluoroacetoxylation of Alkenes

Helena M. Lovick et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2010)

Review Chemistry, Medicinal

Synthesis of Marine Polycyclic Polyethers via Endo-Selective Epoxide-Opening Cascades

Ivan Vilotijevic et al.

MARINE DRUGS (2010)

Article Chemistry, Medicinal

Escape from Flatland: Increasing Saturation as an Approach to Improving Clinical Success

Frank Lovering et al.

JOURNAL OF MEDICINAL CHEMISTRY (2009)

Article Chemistry, Organic

Tethered Aminohydroxylation (TA) Reaction of Amides

Timothy J. Donohoe et al.

ORGANIC LETTERS (2009)

Review Chemistry, Multidisciplinary

Function-oriented synthesis, step economy, and drug design

Paul A. Wender et al.

ACCOUNTS OF CHEMICAL RESEARCH (2008)

Article Chemistry, Multidisciplinary

Asymmetric iodocyclization catalyzed by Salen-Cr-III Cl: Its synthetic application to swainsonine

Hyo Young Kwon et al.

CHEMISTRY-A EUROPEAN JOURNAL (2008)

Review Chemistry, Multidisciplinary

Stereocontrolled synthesis of tetrasubstituted olefins

Alison B. Flynn et al.

CHEMICAL REVIEWS (2007)

Article Chemistry, Physical

Mechanism of cis/trans equilibration of alkenes via iodine catalysis

SS Hepperle et al.

JOURNAL OF PHYSICAL CHEMISTRY A (2005)

Review Chemistry, Multidisciplinary

Intramolecular dipolar cycloaddition reactions of azomethine ylides

I Coldham et al.

CHEMICAL REVIEWS (2005)