98746-58-8

Upstream product

• 908094-04-2 phenyldiazomethane 
• 98-83-9 isopropenylbenzene 
• 65051-83-4 3-methyl-3-phenylcyclopropene 
• 1078-58-6 diphenylzinc 
• 98-80-6 phenylboronic acid 
• 55091-64-0 1-methyl-1-phenyl-2-bromocyclopropane 
• 98-86-2 acetophenone 
• 591-50-4 iodobenzene 
• 17343-73-6 (2,2-dibromo-1-methylcyclopropyl)benzene 

Relevant academic research and scientific papers

Copper-catalyzed diastereo- and enantioselective desymmetrization of cyclopropenes: Synthesis of cyclopropylboronates

A novel Cu-catalyzed diastereo- and enantioselective desymmetrization of cyclopropenes to afford nonracemic cyclopropylboronates is described. Trapping the cyclopropylcopper intermediate with electrophilic amines allows for the synthesis of cyclopropylaminoboronic esters and demonstrates the potential of the approach for the synthesis of functionalized cyclopropanes.

Rhodium-Catalyzed Arylation of Cyclopropenes Based on Asymmetric Direct Functionalization of Three-Membered Carbocycles

A variety of highly diastereo- and enantiomerically enriched arylcyclopropanes is obtained through the asymmetric rhodium-catalyzed arylation reaction of achiral nonfunctionalized cyclopropene derivatives with commercially available aryl boronic acids in the presence of (R,S)-Josiphos.

Asymmetric Copper-Catalyzed Carbozincation of Cyclopropenes en Route to the Formation of Diastereo- and Enantiomerically Enriched Polysubstituted Cyclopropanes

The enantioselective synthesis of cyclopropylzinc reagents has been achieved via a copper-catalyzed carbozincation of 3,3-disubstituted cyclopropenes with diorganozinc reagents. The obtained organozinc compounds can be easily functionalized with a broad range of electrophiles, including palladium-catalyzed cross-couplings, affording highly substituted cyclopropanes. The operationally simple procedure using very low quantities of a commercially available and inexpensive copper catalyst provides a new tool for the synthesis of highly enantioenriched cyclopropanes as single diastereoisomers.

Electronically tuned chiral ruthenium porphyrins: Extremely stable and selective catalysts for asymmetric epoxidation and cyclopropanation

We report the use of three enantiomerically pure and electronically tuned ruthenium carbonyl porphyrin catalysts for the asymmetric cyclopropanation and epoxidation of a variety of olefinic substrates. The D4-symmetric ligands carry a methoxy, a methyl or a trifluoromethyl group at the 10-position of each of the 9-[anti-(1,2,3,4,5,6,7,8-octahydro-1,4:5,8-dimethanoanthracene)]-substituents at the meso-positions of the porphyrin. Introduction of a CF 3-substituent in this remote position resulted in greatly improved catalyst stability, and turnover numbers of up to 7500 were achieved for cyclopropanation, and up to 14200 for epoxidation, with ee values typically >90% and ≈80%, respectively. In one example, the axial CO ligand at the ruthenium was exchanged for PF3, resulting in the first chiral ruthenium porphyrin with a PF3 ligand reported to date. In cyclopropanations with ethyl diazoacetate, the latter catalyst performed exceedingly well, and gave a 95% ee in the case of 1,1-diphenylethylene as substrate.