72397-56-9

Upstream product

• 77-78-1 dimethyl sulfate 
• 180322-84-3 monomethyl (1S,2R)-2-phenylcyclopropane-1,1-dicarboxylate 
• 100-42-5 styrene 
• 108-59-8 malonic acid dimethyl ester 
• 186581-53-3 diazomethane 
• 3376-23-6 C-phenyl-N-methylnitrone 
• 3709-20-4 dimethyl 2-phenyl-1,1-cyclopropanedicarboxylate 
• 1122573-49-2 (1R,2R)-methyl 2-phenyl-1-(pyrrolidin-1-ylcarbonyl)cyclopropanecarboxylate 
• 145838-86-4 bis(methoxycarbonyl)(phenyliodinio)methanide 
• 6773-29-1 dimethyl diazomalonate 
• 278169-72-5 (R)-phenyl-1,2-bis(methanesulfonyloxy)ethane 
• 16355-00-3 (R)-1-phenyl-1,2-ethanediol 
• 67-56-1 methanol 
• 180322-87-6 1-(methoxycarbonyl)-2-phenylcyclopropanecarboxylic acid 

Downstream Products

• 1011725-36-2 (2S,4aS)-dimethyl 1-benzoyl-2-phenyl-2,3-dihydro-1H-pyridazino[1,6-a]quinoline-4,4(4aH)-dicarboxylate 
• 1011725-37-3 (2S,4aR)-dimethyl 1-benzoyl-2-phenyl-2,3-dihydro-1H-pyridazino[1,6-a]quinoline-4,4(4aH)-dicarboxylate 
• 871949-73-4 2-(4-methoxyphenyl)-5-phenyltetrahydrofuran-3,3-dicarboxylic acid dimethyl ester 
• 1130594-00-1 C₂₁H₂₂O₆ 
• 1192554-01-0 C₁₆H₁₈O₅ 
• 1432791-40-6 C₂₇H₃₅NO₄Si 
• 188488-71-3 (-)-methyl 4-[N-(4-methoxyphenyl)amino]-4-phenylbutanoate 

Relevant academic research and scientific papers

Stereospecific copper(II)-catalyzed tandem ring opening/oxidative alkylation of donor-acceptor cyclopropanes with hydrazones: Synthesis of tetrahydropyridazines

Aerobic copper(II)-catalyzed tandem ring opening and oxidative C-H alkylation of donor-acceptor cyclopropanes with bisaryl hydrazones is accomplished to produce tetrahydropyridazines, in which copper(II) plays dual role as a Lewis acid as well as redox catalyst. The reaction is stereospecific, and optically active cyclopropanes can be reacted with high optical purities (89-98% enantiomeric excess). The substrate scope, functional group tolerance, dual role of the copper(II) catalyst, and the use of air as an oxidant are the important practical features. A product bearing a 3-bromoaryl group can be subjected to Pd-catalyzed Suzuki coupling with boronic acid in high yield.

Tetrahydro-1,3-oxazepines via Intramolecular Amination of Cyclopropylmethyl Cation

An efficient synthesis of tetrahydro-1,3-oxazepines was developed involving the regioselective intramolecular amination of cyclopropylmethyl cation. The cation was generated by the abstraction of one imidate group in bis-imidate bearing a carbocation-stabilizing substituent. Using 1,1,2,3-tetrasubstituted cyclopropane substrates, highly diastereoselective intramolecular amination to trans-tetrahydro-1,3-oxazepines was achieved. The resulting tetrahydro-1,3-oxazepines were transformed to the homoallylamine derivatives in high yields.

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.

Asymmetric cyclopropanation of alkenes with dimethyl diazomalonate catalyzed by chiral diene-rhodium complexes

Chiral tridentate ligand : A chiral dienerhodium complex (1; see scheme) was found to catalyze the intermolecular asymmetric cyclopropanation of alkenes with dimethyl diazomalonate to give 1,1-cyclopropane diesters in good yields and with high enantioselectivity.

First X-ray structure of a N-naphthaloyl-tethered chiral dirhodium(II) complex: Structural basis for tether substitution improving asymmetric control in olefin cyclopropanation

Good-ee! The first one-pot olefin cyclopropanation that gives high ee is reported. The optimized catalyst is the 4-Br-substituted chiral paddle-wheel tetracarboxylatodirhodium(II) complex based on N-naphthaloyl-(S)-tert-leucinate. X-ray structural analysis of the parent catalyst reveals a square chiral crown cavity shrouding the axial coordination site (see figure) Figure Presentation

trans-directing ability of the amide group: Enabling the enantiocontrol in the synthesis of 1,1-dicarboxy cyclopropanes. Reaction development, scope, and synthetic applications

(Chemical Equation Presented) In this article, we describe our efforts toward the enantioselective formation of 1,1-cyclopropane diesters via the metal-catalyzed cyclopropanation of olefins. The strategies envisioned to achieve such a goal are discussed a

trans-directing ability of amide groups in cyclopropanation: Application to the asymmetric cyclopropanation of alkenes with diazo reagents bearing two carboxy groups

(Chemical Equation Presented) Highly stereoselective: A highly enantioselective (up to 97 % ee) and diastereoselective (>30:1 d.r.) Rh II-catalyzed cyclopropanation of alkenes using a diazo reagent bearing two carboxy groups is described. This new methodology exploits the powerful trans-directing ability of amides to improve enantiocontrol. Mono- and disubstituted olefins are cyclopropanated in good yields. nttl=N-1,8-naphthoyl- tert-leucine.

Cycloadditions of aromatic azomethine imines with 1,1-cyclopropane Diesters

The cycloaddition of aromatic azomethine imines to 1,1-cyclopropane diesters was achieved using Ni(CIO4)2 as catalyst. The methodology gives access to unique tricyclic dihydroquinoline derivatives with dr up to 6.6:1. A nonconcerted

GaCl3-catalyzed insertion of diazene derivatives into the cyclopropane ring

(Chemical Equation Presented) GaCl3 has been found to efficiently catalyze the formal cycloadditions of diazene derivatives 6 onto 2-arylcyclopropane-1,1-dicarboxylates 5, giving rise to the pyrazolidine derivatives 7. The insertion into the cy

The cycloaddition of nitrones with homochiral cyclopropanes

(Chemical Equation Presented) The cycloaddition of nitrones and enantiomerically pure cyclopropane-1,1-dicarboxylates is examined. Transfer of optical activity to the adduct is dictated by thermal reaction conditions and nature of cyclopropane substitutio