Gold(I)-catalyzed enantioselective polycyclization reactions.

J Am Chem Soc

Department of Chemistry, University of California, Berkeley, California 94720, USA.

Published: June 2010

A series of enantioselective polycyclization reactions, catalyzed by a cationic bisphosphine gold complexes, are described. The polycyclization reactions, which employ an alkyne as an initiating group, begin with a gold-promoted 6-exo-dig cyclization and can be terminated with a variety of nucleophiles including carboxylic acids, phenols, sulfonamides, and electron-rich aryl groups. This method allows for the preparation of up to four bonds in a single operation with excellent diastereo- and enantioselectivity.

Download full-text PDF

Source
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC2888676PMC
http://dx.doi.org/10.1021/ja103544pDOI Listing

Publication Analysis

Top Keywords

polycyclization reactions
12
enantioselective polycyclization
8
goldi-catalyzed enantioselective
4
reactions series
4
series enantioselective
4
reactions catalyzed
4
catalyzed cationic
4
cationic bisphosphine
4
bisphosphine gold
4
gold complexes
4

Similar Publications

Synthesis and Optical Properties of -Arylnaphtho- and Anthra[2,3-]oxazol-2-amines.

Molecules

January 2025

School of Pharmaceutical Sciences, Aichi Gakuin University, 1-100 Kusumoto-cho, Chikusa-ku, Nagoya 464-8650, Japan.

Oxazole, a versatile and significant heteroarene, serves as a bridge between synthetic organic chemistry and applications in the medicinal, pharmaceutical, and industrial fields. Polycyclic aromatic compounds with amino groups substituted at the 2-position of an oxazole, such as 2-aminonaphthoxazoles, are expected to be functional probes, but their synthetic methods are extremely limited. Herein, we describe electrochemical reactions of 3-amino-2-naphthol or 3-amino-2-anthracenol and isothiocyanates in DMSO, using a graphite electrode as an anode and a platinum electrode as a cathode in the presence of potassium iodide (KI), which afford -arylnaphtho- and -arylanthra[2,3-]oxazol-2-amines via cyclodesulfurization.

View Article and Find Full Text PDF

Nitrogen-containing heterocycles, such as indoles and quinolines, serve as the key scaffolds in numerous pharmaceuticals, pesticides, and natural products. The synthesis methods of nitrogen-containing heterocycles show significant scientific and industrial value. As a chemical intermediate featuring dual functional groups, cyanamide plays a crucial role in organic synthesis, directly affecting the development of new drugs and the design of new materials.

View Article and Find Full Text PDF

Aggregation-caused quenching (ACQ) reduces luminescence and compromises brightness in solid-state displays, necessitating strategies to mitigate its effects for enhanced performance. This study presents cost-effective method to mitigate ACQ of pyrene by co-assembling polycyclic aromatic hydrocarbons within low molecular weight gelator. ​Synthesized from readily available materials-cholesteryl chloroformate and pentaerythritol-in one-step reaction, gelator incorporates four cholesteryl units, reported to promote robust supramolecular gels in various solvents.

View Article and Find Full Text PDF

Reactivity of Anomalous Aziridines for Versatile Access to High Fsp Amine Chemical Space.

Acc Chem Res

January 2025

Department of Chemistry, University of Wisconsin, 1101 University Avenue, Madison, Wisconsin 53706, United States.

ConspectusThe manipulation of strained rings is a powerful strategy for accessing the valuable chemical frameworks present in natural products and active pharmaceutical ingredients. Aziridines, the smallest N-containing heterocycles, have long served as building blocks for constructing more complex amine-containing scaffolds. Traditionally, the reactivity of typical aziridines has been focused on ring-opening by nucleophiles or the formation of 1,3-dipoles.

View Article and Find Full Text PDF

Dearomatizing Photocyclization and Oxidative Aromatization: Constructing Polycyclic Arenes from Styrenes.

Chem Asian J

January 2025

Xiamen University, Department of Chemistry, Xiamen University, Lujiaxi Building Room 742, 361005, xiamen, CHINA.

The direct construction of polycyclic arenes through ring formation using simple building blocks is highly appealing but remains challenging in organic chemistry. In this study, we introduce an efficient cascade reaction that combines dearomatizing photocyclization with oxidative aromatization, driven by organophotocatalysis. Conducted under mild, transition-metal-free conditions, this reaction seamlessly converts styrene derivatives into a diverse array of functionalized polycyclic aromatic compounds with good yields and regioselectivity.

View Article and Find Full Text PDF

Want AI Summaries of new PubMed Abstracts delivered to your In-box?

Enter search terms and have AI summaries delivered each week - change queries or unsubscribe any time!