193079-04-8

Upstream product

• 100-42-5 styrene 
• 119987-21-2 (E)-methyl 2-diazo-4-phenylbut-3-enoate 
• 118575-70-5 trans-styrylacetyl chloride 
• 152978-83-1 (3R)-3-(4,4-dimethyl-2-oxotetrahydrofuranyl) (E)-4-phenyl-3-butenoate 
• 153062-67-0 (3R)-3-(4,4-dimethyl-2-oxotetrahydrofuranyl) (E)-2-diazo-4-phenyl-3-butenoate 
• 2243-53-0 trans-styrylacetic acid 
• 119987-21-2 methyl α-styryl-α-diazoacetate 
• 138770-13-5 (3R)-3-(4,4-dimethyl-2-oxotetrahydrofuranyl) 2α-phenyl-1α-((E)-2-phenylethenyl)-1β-cyclopropanecarboxylate 

Downstream Products

• 180322-84-3 monomethyl (1S,2R)-2-phenylcyclopropane-1,1-dicarboxylate 

Relevant academic research and scientific papers

Studies of asymmetric styrene cyclopropanation with a rhodium(II) metallopeptide catalyst developed with a high-throughput screen

Dirhodium metallopeptides have been developed as selective catalysts for asymmetric cyclopropanation reactions. A selective ligand sequence has been identified by screening on-bead metallopeptide libraries in a 96-well plate format. Efficient ligand synthesis and screening allows a 200-member library to be created and assayed in less than three weeks. These metallopeptides catalyze efficient cyclopropanation of aryldiazoacetates, providing asymmetric access to cyclopropane products in high diastereoselectivity. 2013 Wiley Periodicals, Inc.

Determination of orientational isomerism in rhodium(II) metallopeptides by pyrene fluorescence

Rhodium(II) metallopeptides display useful secondary structure, self-assembly, and catalytic activity. The bis-peptide complexes exhibit subtle orientational isomerism that affects function, but is challenging to characterize. We report that pyrene excime

Determination of orientational isomerism in rhodium(II) metallopeptides by pyrene fluorescence

Rhodium(II) metallopeptides display useful secondary structure, self-assembly, and catalytic activity. The bis-peptide complexes exhibit subtle orientational isomerism that affects function, but is challenging to characterize. We report that pyrene excime

D 2-symmetric dirhodium catalyst derived from a 1,2,2-triarylcyclopropanecarboxylate ligand: Design, synthesis and application

Dirhodium tetrakis-(R)-(1-(4-bromophenyl)-2,2- diphenylcyclopropanecarboxylate) (Rh2(R-BTPCP)4) was found to be an effective chiral catalyst for enantioselective reactions of aryl- and styryldiazoacetates. Highly enantioselective cyclopropanations, tandem cyclopropanation/Cope rearrangements and a combined C-H functionalization/Cope rearrangement were achieved using Rh2(R-BTPCP)4 as catalyst. The advantages of Rh2(R-BTPCP)4 include its ease of synthesis, its tolerance to the size of the ester group in the styryldiazoacetates, and its compatibility with dichloromethane as solvent. Computational studies suggest that the catalyst adopts a D2-symmetric arrangement, but when the carbenoid binds to the catalyst, two of the p-bromophenyl groups on the ligands rotate outward to make room for the carbenoid and the approach of the substrate to the carbenoid.

Dirhodium tetraprolinate-catalyzed asymmetric cyclopropanations with high turnover numbers

(Matrix presented) The bridged dirhodium tetraprolinate Rh 2(S-biTISP)2 (2) catalyzes the asymmetric cyclopropanation reaction between methyl phenyldiazoacetate and styrene at room temperature with high turnover number (92 000) and t

A rigid dirhodium(II) carboxylate as an efficient catalyst for the asymmetric cyclopropanation of olefins

The dirhodium(II) complex 7 of (1S,3R,4R)-2-(p-tert-butylphenylsulphonyl)-2-aza-bicyclo[2.2.1]heptane-3- carboxylic acid (3) (or its enantiomer) was synthesised in four steps from cyclopentadiene, (R)- or (S)-phenylethylamine and methyl glyoxylate. Comple

Novel dirhodium tetraprolinate catalysts containing bridging prolinate ligands for asymmetric carbenoid reactions

The D2-symmetric dirhodium prolinate complex 3 is an effective catalyst for asymmetric vinylcarbenoid and phenylcarbenoid cyclopropanations.

Synthesis and evaluation of a novel dirhodium tetraprolinate catalyst containing bridging prolinate ligands

The D2 symmetric dirhodium prolinate complex 2 is an effective catalyst for asymmetric vinylcarbenoid cyclopropanations.

Asymmetric cyclopropanations by rhodium(II) N-(arylsulfonyl)prolinate catalyzed decomposition of vinyldiazomethanes in the presence of alkenes. Practical enantioselective synthesis of the four stereoisomers of 2-phenylcyclopropan-1-amino acid

The rhodium N-(arylsulfonyl)prolinate catalyzed decomposition of vinyldiazomethanes in the presence of alkenes leads to a very general method for the synthesis of functionalized cyclopropanes in a highly diastereoselective and enantioselective mode. A det

Effect of diazoalkane structure on the stereoselectivity of rhodium(II) (S)-N-(arylsulfonyl)prolinate catalyzed cyclopropanations

Rhodium(II) (S)-N-(arylsulfonyl)prolinate catalyzed decomposition of diazoalkanes containing a methyl ester and either a vinyl or a phenyl group in the presence of alkenes results in highly diastereoselective and enantioselective cyclopropanations.