Chiral α-aminophosphonates with adjacent carbon and phosphonate stereogenic centers have been employed as ligands in the copper-catalyzed oxidative coupling of 2-naphthols, resulting in the production of chiral BINOLs in favorable yields and moderate to good enantiomeric excess. This represents the first application of chiral P-based ligands to enable such a transformation. The synthesis of these chiral α-aminophosphonate ligands offers a significant advantage over approaches that typically necessitate elaborate synthetic processes for chiral ligand production.
Download full-text PDF |
Source |
|---|---|
| http://dx.doi.org/10.1021/acs.orglett.4c01582 | DOI Listing |
Publication Analysis
Top Keywords
Similar Publications
Chemodivergent, enantio- and regioselective couplings of alkynes, aldehydes and silanes enabled by nickel/N-heterocyclic carbene catalysis.
Sci Bull (Beijing)
December 2024
State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, Chinese Academy of Sciences, Shanghai 200032, China. Electronic address:
Divergent synthesis of valuable molecules through common starting materials and metal catalysis represents a longstanding challenge and a significant research goal. We here describe chemodivergent, highly enantio- and regioselective nickel-catalyzed reductive and dehydrogenative coupling reactions of alkynes, aldehydes, and silanes. A single chiral Ni-based catalyst is leveraged to directly prepare three distinct enantioenriched products (silyl-protected trisubstituted chiral allylic alcohols, oxasilacyclopentenes, and silicon-stereogenic oxasilacyclopentenes) in a single chemical operation.
View Article and Find Full Text PDFChiral Nanostructures from Artificial Helical Polymers: Recent Advances in Synthesis, Regulation, and Functions.
ACS Nano
January 2025
School of Science and Engineering, Shenzhen Institute of Aggregate Science and Technology, The Chinese University of Hong Kong, Shenzhen (CUHK-Shenzhen), Guangdong 518172, P.R. China.
Helical structures such as right-handed double helix for DNA and left-handed α-helix for proteins in biological systems are inherently chiral. Importantly, chirality at the nanoscopic level plays a vital role in their macroscopic chiral functionalities. In order to mimic the structures and functions of natural chiral nanoarchitectures, a variety of chiral nanostructures obtained from artificial helical polymers are prepared, which can be directly observed by atomic force microscopy (AFM), scanning tunneling microscopy (STM), scanning electron microscopy (SEM), and transmission electron microscopy (TEM).
View Article and Find Full Text PDFA modular approach to catalytic stereoselective synthesis of chiral 1,2-diols and 1,3-diols.
Nat Commun
January 2025
The Institute for Advanced Studies and Hongyi Honor College, Wuhan University, Wuhan, China.
Optically pure 1,2-diols and 1,3-diols are the most privileged structural motifs, widely present in natural products, pharmaceuticals and chiral auxiliaries or ligands. However, their synthesis relies on the use of toxic or expensive metal catalysts or suffer from low regioselectivity. Catalytic asymmetric synthesis of optically pure 1,n-diols from bulk chemicals in a highly stereoselective and atom-economical manner remains a formidable challenge.
View Article and Find Full Text PDFStereoselective amino alcohol synthesis via chemoselective electrocatalytic radical cross-couplings.
Nat Chem
January 2025
Department of Chemistry, Scripps Research, La Jolla, CA, USA.
Amino alcohols are vital in natural products, pharmaceuticals and agrochemicals, and as key building blocks for various applications. Traditional synthesis methods often rely on polar bond retrosynthetic analysis, requiring extensive protecting group manipulations that complicate direct access. Here we show a streamlined approach using a serine-derived chiral carboxylic acid in stereoselective electrocatalytic decarboxylative transformations, enabling efficient access to enantiopure amino alcohols.
View Article and Find Full Text PDFWant 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!