A5066429252- Synthetic Organic Chemistry Methods
- Chemical Synthesis and Analysis
- Asymmetric Hydrogenation and Catalysis
- Asymmetric Synthesis and Catalysis
- Organometallic Complex Synthesis and Catalysis
- Organoboron and organosilicon chemistry
- X-ray Diffraction in Crystallography
- Crystallization and Solubility Studies
- Organic and Inorganic Chemical Reactions
University of Michigan
2018-2022
The development of a Lewis acid-catalyzed ring-opening cross-metathesis reaction which enables selective access to acyclic, unsaturated ketones as the carbonyl–olefin metathesis products is described. While catalytic amounts FeCl3 were previously identified optimal catalyze ring-closing reactions, complementary between cyclic alkenes and carbonyl functionalities relies on GaCl3 superior acid catalyst.
An intermolecular carbonyl-olefin metathesis reaction is described that relies on superelectrophilic Fe(III)-based ion pairs as stronger Lewis acid catalysts. This new catalytic system enables selective access to (E)-olefins products. Mechanistic investigations suggest the regioselective formation and stereospecific fragmentation of intermediate oxetanes be origin this selectivity. The optimized conditions are general for a variety aryl aldehydes trisubstituted olefins demonstrated 28...
Herein we describe the application of Lewis-acid-catalyzed carbonyl-olefin metathesis toward synthesis substituted tetrahydropyridines from commercially available amino acids as chiral pool reagents. This strategy relies on FeCl3 an inexpensive and environmentally benign catalyst enables access to a variety under mild reaction conditions. The proceeds with complete stereoretention is viable for natural unnatural provide corresponding in up 99% yield.
In carbonyl–olefin metathesis, two π-bonds undergo a cycloaddition-cycloreversion process to form valuable alkenes from simple precursors. Although this synthetic methodology has advanced significantly, further improvements would be greatly facilitated by clear understanding of whether Lewis-acid-catalyzed metathesis reactions occur via stepwise or concerted pathway. Here we use 12C/13C kinetic isotope effects (KIEs), 1H/2H KIEs, and Hammett studies show that prototypical iron(III)-catalyzed...
Herein, we describe the application of Lewis acid-catalyzed carbonyl-olefin metathesis towards synthesis chiral, substituted tetrahydropyridines from commercially available amino acids as chiral pool reagents. This strategy relies on FeCl 3 an inexpensive and environmentally benign catalyst enables access to a variety under mild reaction conditions. The proceeds with complete stereoretention is viable for natural unnatural provide corresponding in up 99% yield.
<div> <p>Herein, we describe the application of Lewis acid-catalyzed carbonyl-olefin metathesis towards synthesis chiral, substituted tetrahydropyridines from commercially available amino acids as chiral pool reagents. This strategy relies on FeCl<sub>3</sub> an inexpensive and environmentally benign catalyst enables access to a variety under mild reaction conditions. The proceeds with complete stereoretention is viable for natural unnatural provide corresponding in...