Study of the origin of enantioselectivity in cyclopropanation reactions using the chiral iron carbene complex [(η5-C5H5)(CO)2FeCH[(η6-o-MeOC6H4)Cr(CO)3]]+

Wang, Qinwei; Försterling, F. Holger; Hossain, M. Mahmun

doi:10.1016/j.jorganchem.2005.09.025

Cited by 12 publications

(3 citation statements)

References 20 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Synthesis and reactions of allenylidene iron complexes with nucleophiles was reported [1608]. Chiral cationic iron carbene complexes participated in cis-and enantioselective cyclopropanations of unactivated alkenes [1609]. Tungsten acetylide complexes react with iminium ions to form alkenyl carbenes [1610].…”

Section: Reactions Of Isolated Transitionmetal Complexes and Copper-mentioning

confidence: 99%

Transition metals in organic synthesis: Highlights for the year 2005

Söderberg

2008

Coordination Chemistry Reviews

View full text Add to dashboard Cite

Section: Reactions Of Isolated Transitionmetal Complexes and Copper-mentioning

confidence: 99%

Transition metals in organic synthesis: Highlights for the year 2005

Söderberg

2008

Coordination Chemistry Reviews

View full text Add to dashboard Cite

“…enantiomeric ratio determined by chiral HPLC using a Chiralpak-OJ-H column (Hexane 100%, 1 mL/min): τmajor= 12.9 min, τminor= 11.5 min. Data are in agreement with literature data [8] .…”

Section: Synthesis Of 1-methoxy-4-((1r2s)-2-phenylcyclopropyl)benzene (4c)supporting

confidence: 92%

Modular Enantioselective Synthesis of cis-Cyclopropanes through Self-Sensitized Stereoselective Photodecarboxylation with Benzothiazolines

View full text Add to dashboard Cite

“…This isolated compound was then treated with trimethylsilyl triflate, generating a chiral iron carbene intermediate (153) that promptly reacted with an alkene in solution to form the desired cyclopropane (154) in cis/trans -ratios above 6:1 and exceptional enantioselectivity (ee > 95%). Exposure to natural sunlight was then sufficient to dissociate the chromium complex and obtain the final product (155) , a precursor to the antibiotic cilastatin. − …”

Section: Alternative Approaches Toward Iron Carbenesmentioning

confidence: 99%

Iron: A Worthy Contender in Metal Carbene Chemistry

2020

View full text Add to dashboard Cite

Carbene transfer reactions hold a pivotal role in organic synthesis, allowing the prompt construction of complex molecules from accessible reagents. Iron complexes emerged as promising catalysts for this reaction, rivaling noble metals' reactivity with improved environmental sustainability and lower costs. Herein, we thoroughly examine the development of iron-catalyzed methodologies in the last 30 years, showcasing its broad reactivity and room for further improvement. Aside from the well-known iron complexes of tetrapyrrolic ligands, recent developments on other iron catalysts are emphasized.

show abstract

Study of the origin of enantioselectivity in cyclopropanation reactions using the chiral iron carbene complex [(η5-C5H5)(CO)2FeCH[(η6-o-MeOC6H4)Cr(CO)3]]+

Cited by 12 publications

References 20 publications

Transition metals in organic synthesis: Highlights for the year 2005

Transition metals in organic synthesis: Highlights for the year 2005

Modular Enantioselective Synthesis of cis-Cyclopropanes through Self-Sensitized Stereoselective Photodecarboxylation with Benzothiazolines

Iron: A Worthy Contender in Metal Carbene Chemistry

Contact Info

Product

Resources

About