AI Article Synopsis
- The iron(III) chiral porphyrin Fe(2)(OMe) demonstrates high catalytic activity in cyclopropanation reactions, showing strong selectivity with trans-diastereoselectivities of up to 99:1 and enantioselectivities of 87%.
- The catalyst exhibits impressive turnover numbers (TON) and turnover frequencies (TOF), reaching values of 10,000 and 120,000 h(-1), indicating both its effectiveness and stability under optimized experimental conditions.
- The study explored the structural components of the porphyrin and the role of methoxy ligands, using DFT calculations to enhance understanding of the mechanistic processes involved in the carbene transfer reaction.
Article Abstract
The catalytic activity of the iron(III) C2 chiral porphyrin Fe(2)(OMe) in alkene cyclopropanation is herein reported. The catalyst promoted the reaction of differently substituted styrenes with diazo derivatives with trans-diastereoselectivities and enantioselectivities up to 99:1 and 87 %, respectively. In addition, high TON and TOF values (up to 10 000 and 120 000 h(-1) , respectively) were observed indicating good activity and stability of the catalyst in optimized experimental conditions. The study of the cyclopropanation reaction revealed that the porphyrin skeleton is composed of two 'totem' parts which were independently responsible for the observed enantio- and diastereoselectivities. To further our research we also investigated the catalytic role of the methoxy axial ligand coordinated to the iron atom. The molecular structure of Fe(2)(OMe) was optimized by DFT calculations which were also employed to achieve a better understanding of the mechanistic details of the carbene transfer reaction.
Download full-text PDF |
Source |
|---|---|
| http://dx.doi.org/10.1002/chem.201602289 | DOI Listing |
Publication Analysis
Top Keywords
Similar Publications
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!