105367-36-0

Upstream product

• 100-42-5 styrene 
• 63254-50-2 L-menthyl diazoacetate 
• 2216-51-5 (-)-menthol 
• 939-89-9 (1S)-2-phenylcyclopropane-1-carboxylic acid 
• 65437-23-2 d-menthyl diazoacetate 

Downstream Products

• 23020-15-7 (1S,2S)-2-phenylcyclopropane-1-carboxylic acid 

Relevant academic research and scientific papers

Asymmetric cyclopropanation and aziridination reactions of olefins catalyzed by Cu(I)-binaphthyldiimine complexes

The chiral Cu(I)-N,N′-bis(2,6-dichlorobenzylidene)-1,1′-binaphthyl-2, 2′-diamine complex was found to be an efficient catalyst for asymmetric cyclopropanation and aziridination reactions of olefins with l-menthyl diazoacetate and [N-(p-tolylsulfonyl)imino

Synthesis of chiral bis(oxazolinyl)biferrocene ligands and their application to Cu(I)-catalyzed asymmetric cyclopropanation

Homochiral bis(oxazolinyl)biferrocene ligands, which have both planar and central chirality, are synthesized from oxazolinylferrocenes through a diastereoselective directed lithiation followed by an oxidative dimerization. Asymmetric cyclpropanation of styrene with diazoacetates in the presence of 5 mol% CuOTf-bis(oxazolinyl)biferrocene complexes gives 2-(phenyl)cyclopropane carboxylates in up to 99% ee.

Cu(I)-binaphthyldiimine catalyzed asymmetric cyclopropanation of olefin with diazoacetate

Chiral 1,1′-binaphthyl-N,N′-bis(2,6-dichloro-benzy-lidene)-2,2′- diamine (1) was found to be an effective ligand for the copper-catalyzed enantioselective cyclopropanation of olefin with l-menthyl diazoacetate. For example, the reaction of 1,1-diphenyleth

Synthesis of an Axially Dissymmetric Biphenylcarboxylate Ligand, BDME, and Asymmetric Cyclopropanation of Olefins with Diazoacetate Catalyzed by Its Dirhodium(II) Complex

An axially dissymmetric biphenylcarboxylate ligand, BDME (4), has been newly designed and prepared. The dirhodium(II) complex (1) of (4) proved to be an excellent catalyst in asymmetric cyclopropanation of styrene with d-menthyl diazoacetate affording d-menthyl cis- 2- phenyl-cyclopropane-1-carboxylate of 99% de.

Novel chiral bisoxazoline ligands with a biphenyl backbone: Preparation, complexation, and application in asymmetric catalytic reactions

Novel C2-symmetric chiral bisoxazoline ligands 1 were easily prepared from enantiomerically pure 2-amino alcohols and achiral 2,2′-biphenyldicarboxylic acid via the corresponding amide and mesylate as intermediates. Since these ligands bear only two ortho-substituents on the biphenyl backbone, the biphenyl axis is not fixed, and the two diastereomers of these ligands exist in equilibrium in solution. Interestingly, when the ligands 1 were coordinated with a metal ion, only one of the two possible diastereomer complexes, an (S,aS,S)-complex, can be formed depending on the combination of the ligand and the metal ion. Thus, copper(I) afforded only the (S,a,S,S)-complexes with all ligands 1, while zinc(II), palladium(II), and silver(I) afforded the (S,aS,S)-complexes as the sole product only with 1b, which has a bulky terf-butyl group on the oxazoline ring, and a mixture of the two diastereomer complexes with 1a,c,d. The copper(I)-catalyzed asymmetric cyclopropanation of styrene with diazoacetate proceeded successfully with these ligands and good to excellent enantioselectivities were afforded.

Synthesis of imine-amine type of chiral ligands and their application in the asymmetric cyclopropanation of olefins with diazoacetates

Novel chiral ligands 1, which possess both imine and amine moieties, were prepared from readily available homochiral materials. Copper complexes of 1 were prepared in situ and used in the asymmetric cyclopropanation of olefins with alkyl diazoacetates to

Tetrakisdirhodium(II) and Its Catalytic Applications for Metal Carbene Transformations

The synthesis and X-ray structure of the binuclear complex tetrakisdirhodium(II) (4>) are reported.Structure-selectivity comparisons are made for typical metal carbene transformations, such as inter- and intramolecular cyclopropane formation, intermolecular cyclopropene formation and intramolecular C-H insertions of diazoacetates and diazoacetamides.The enantioselectivity achieved in the 4>-catalyzed reactions is intermediate between that of 4> and 4>, which were described previously (mepy=methyl 5-oxopyrrolidine-2-carboxylate; bnox=4-benzyloxazolidin-2-one).In contrast to other catalyzed intermolecular cyclopropane formations, those using 4> result preferentially in formation of the cis-cyclopropane.

Bisoxazoline ligands with an axial-unfixed biaryl backbone: the effects of the biaryl backbone and the substituent at oxazoline ring on Cu-catalyzed asymmetric cyclopropanation

The synthesis of novel C2-symmetric bisoxazoline ligands with an axial-unfixed biaryl backbone and different substituents at the oxazoline ring is reported. The diastereomer equilibrium of these ligands in solution and their complexation behavi

Novel chiral dibenzo[a,c]cycloheptadiene bis(oxazoline) and catalytic enantioselective cyclopropanation of styrene

A series of chiral C2-symmetric bis(oxazoline) ligands containing dibenzo[a,c]cycloheptadiene units were synthesized. The copper complexes, prepared in situ from copper (I)-triflate and the new enantiopure oxazoline ligands, were assessed as chiral catalysts in the enantioselective cyclopropanation of styrene with diazoacetate. Enantioselectivities up to 82 and 62%, respectively, for trans- and cis-2-phenylcyclopropanecarboxylate were observed.

Catalytic asymmetric cyclopropanation of alkenes with diazoesters in protic and biphasic media

As a C2 symmetric hydrophilic chiral ligand, a series of 2,6-bis(oxazolinyl)-pyridines (pyboxs) bearing a hydroxyalkyl group on the oxazoline ring has been synthesized from readily available amino acid derivatives. Catalytic asymmetric intermolecular cyclopropanation of electron rich terminal alkenes with diazoesters in the presence of hydrophilic pybox ligand, pybox-hm and Ru(II) complex proceeded smoothly in protic or biphasic media to give the corresponding cyclopropanation products in 97:3 to 99:1 trans/cis ratios and 90 to 97% ee. In the case of the intramolecular cyclopropanation reaction of trans-cinnamyl diazoester using Ru(II)(pybox-he) complex in biphasic medium gave the corresponding cyclopropane ring fused lactone in 52% ee. Steric tuning of the chiral environment of pybox ligands was simply achieved by using a weak interaction between the solvent and the hydroxyl groups of the chiral ligand. The solubility of the new hydrophilic pybox and Ru(II) complexes in protic solvents is dramatically increased; hence, the efficiency of these catalysts enhanced the rate of cyclopropanation. Furthermore, the active catalyst in the water phase can be re-used several times for the cyclopropanation reaction.