19952-66-0

Upstream product

• 20098-66-2 (+/-)-3-phenyl-cyclopropane-1r,2t-dicarboxylic acid dimethyl ester 
• 785-58-0 3-Phenyl-1,2-cyclopropandicarbonsaeure-dimethylester 
• 103-26-4 Methyl cinnamate 
• 103-36-6 ethyl 3-phenyl-2-propenoate 
• 493-72-1 5-phenyl-cyclohexane-1,3-dione 
• 122-57-6 1-Phenylbut-1-en-3-one 
• 18986-67-9 4-Brom-2,2-dimethyl-5-phenylcyclohexan-1,3-dion 
• 5434-98-0 2,2-dimethyl-5-phenyl-1,3-cyclohexanedione 
• 18986-66-8 methyl 5-phenylcyclohexane-1,3-dione 
• 733-14-2 Diethyl (1RS,2RS,3RS)-3-Phenylcyclopropane-1,2-dicarboxylate 
• 785-58-0 3-phenyl-cyclopropane-1r,2t-dicarboxylic acid dimethyl ester 

Downstream Products

• 20098-66-2 (+/-)-3-phenyl-cyclopropane-1r,2t-dicarboxylic acid dimethyl ester 
• 785-58-0 3-phenyl-cyclopropane-1r,2t-dicarboxylic acid dimethyl ester 

Relevant academic research and scientific papers

Enantioselective Cyclopropanation of 4-Nitroisoxazole Derivatives

The present study reports an asymmetric organocatalytic cascade reaction of 4-nitroisoxazole derivative with α,β-unsaturated aldehydes catalysed by chiral secondary amine. Using this approach, 1,2,3-trisubstituted cyclopropane products were obtained in isolated yields up to 98% with moderate diastereoselectivities, and enantiopurity up to 99% ee. Moreover, this synthetic protocol can be used for further applications, as shown by a set of additional transformations of the corresponding cyclopropanes and by the formal synthesis of GABA ligands. (Figure presented.).

184. Stereoselective Hydrolysis of Substituted Cyclopropanedicarboxylates with Pig Liver Esterase

The hydrolysis of the meso-cyclopropane-1,2-dicarboxylates 1a-3a, 4, 5a, 6a, and 9, containing various substituents at C(3), and of the rac-3-phenylcyclopropane-1,2-dicarboxylates 7a, 8a, and 10 with pig liver esterase (PLE) is described.The stereoselectivity and absolute configurations of the products were determined.An interpretation of results was attempted on the basis of a recent active-site model for PLE.

Cyclopropanediamines, 3. - Pure Diastereomers of 1,2-Cyclopropanedicarboxylic Acids and Derivatives

Efficient preparations of pure diastereomers of dimethyl 1,2-cyclopropanedicarboxylates 2, dicarboxylic acids 3, dicarbonyl dichlorides 4, and dihydrazides 5 are reported.Mixtures of diastereomers of dimethyl dicarboxylates 2a, b, d, e are obtained from α,β-unsaturated methyl carboxylates 7 and methyl α-chlorocarboxylates 8 as well as from 7c, d and the sulfur ylide 10 (2c, d).The diastereomers are separated by fractionating distillations (2a, b, c, e) or crystallization (2d) on a 100-g to 1-kg scale (d.e. >99percent).Only low yields of 2c are obtained in the reaction of methyl crotonate (7c) with methyl α-chloroacetate (8a), since 7c predominantly dimerizes to afford 12.The diesters 2 are converted into the pure diastereomeric diacids 3, dicarbonyl dichlorides 4, and dihydrazides 5. 3,3-Dimethyl-cis-1,2-cyclopropanedicarboxylic acid (cis-3f) is obtained by trans-->cis isomerization of trans-3f with the help of acetic anhydride and sodium acetate as catalyst.The configurations of 2-6 and 12 are confirmed by 1H NMR spectroscopy.Derivatives of cis-1,2-dimethyl-1,2-cyclopropanedicarboxylic acid tend to form bicyclic products.Thus, the reaction of cis-3e with phosphorus pentachloride yields mainly the cyclic anhydride 6e and only small amounts of the dicarbonyl dichloride cis-4e.Furthermore, the dihydrazide cis-5e slowly cyclizes in the solid state to give the N-aminoimide 13 and hydrazine, a reaction which is fast in solution.Pure 13 is obtained by thermolysis of cis-5e at 60-65 deg C under high vacuum.