The asymmetric synthesis of an aryltetralin lignan, (-)-lintetralin, was achieved with an overall yield of 29% with seven steps. Key features of the synthesis are an asymmetric Strecker reaction, a diastereoselective Michael addition of the lithiated amino nitrile product to 5H-furan-2-one, and an intramolecular carbocationic cyclization to provide the desired ring skeleton with the correct configuration.
Download full-text PDF |
Source |
|---|---|
| http://dx.doi.org/10.1002/chir.10242 | DOI Listing |
Publication Analysis
Top Keywords
Similar Publications
Pd-Catalyzed Asymmetric Synthesis of Chiral 2-Trifluoromethyl-4-(indol-3-yl)-4-chromene Derivatives.
J Org Chem
January 2025
State Key Laboratory of Fine Chemicals, Department of Pharmaceutical Engineering, School of Chemical Engineering, Dalian University of Technology, 2 Linggong Road, Dalian 116024, China.
This paper presents a new strategy for the construction of the chiral 4-chromene skeleton. A series of chiral 2-trifluoromethyl-4-(indol-3-yl)-4-chromenes were synthesized in moderate to good yields (60-92%) with excellent enantioselectivity (up to 97% ee) through the palladium-catalyzed asymmetric condensation of 2-chromenes and indoles. These trifluoromethylated, stereochemically rich building blocks hold potential value in medicinal chemistry.
View Article and Find Full Text PDFEnantioselective Catalytic Synthesis of Inherently Chiral Calixarenes.
Chem Rec
January 2025
Chongqing Key Laboratory of Natural Product Synthesis and Drug Research, School of Pharmaceutical Sciences, Chongqing University, Chongqing, 401331, P. R. China.
Since the introduction of the concept of inherent chirality by Böhmer, an important part of research focused on the asymmetric synthesis of calixarene macrocycles. However, long synthetic procedures and tedious separation strategies hampered the application of this technology in many topics of organic chemistry, including enantioselective molecular recognition and catalysis. Very recently, a new generation of enantioselective catalytic methodologies has been reported, able to provide highly functionalized, inherently chiral calixarenes in a straightforward manner.
View Article and Find Full Text PDFEnantioselective synthesis of 2-substituted bicyclo[1.1.1]pentanes via sequential asymmetric imine addition of bicyclo[1.1.0]butanes and skeletal editing.
Nat Chem
January 2025
Shenzhen Grubbs Institute, Department of Chemistry, Southern University of Science and Technology, Shenzhen, China.
The substitution of an aromatic ring with a C(sp)-rich bicyclic hydrocarbon, known as bioisosteric replacement, plays a crucial role in modern drug discovery. Substituted bicyclo[1.1.
View Article and Find Full Text PDFEnantioselective Borylcupration/Cyclization of Alkene-Tethered Oxime Esters.
Angew Chem Int Ed Engl
January 2025
University of Toronto, Dept. of Chemistry, 80 St. George Street, M5S 3H6, Toronto, CANADA.
A copper-catalyzed enantioselective synthesis of borylated 1-pyrrolines from γ,δ-unsaturated oxime esters is reported. Twenty-four novel 1-pyrroline derivatives are reported in yields ranging from 26% to 96% and enantioselectivities from 74.5:25.
View Article and Find Full Text PDFMAdPHOS, a P-Stereogenic Aminodiphosphane Ligand with Adamantyl Groups: Synthesis, NH/PH Tautomerism, and Rhodium and Nickel Complexes.
J Org Chem
January 2025
Institute for Research in Biomedicine (IRB Barcelona). The Barcelona Institute of Science and Technology (BIST), Baldiri Reixach 10, 08028 Barcelona, Spain.
A novel chiral ligand, named MAdPHOS, bearing a P-stereogenic phosphane and a diadamantyl phosphane linked by a NH bridge has been synthesized. This bulky, C-symmetric, PNP ligand has been prepared from enantiopure -butylmethyl aminophosphane and was obtained as a crystalline solid. The NH/PH tautomerism, air-stability, and σ-donor capacity of MAdPHOS have been assessed herein.
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!