110716-95-5

Usage

Uses

Used in Drug Development:
(2R,3R)-(Z)-cyclo-Phenylalanine is used as a building block for the synthesis of novel pharmaceutical compounds due to its unique structure and potential biological activities.
Used in Medicinal Chemistry:
(2R,3R)-(Z)-cyclo-Phenylalanine is used as a chiral synthon for the development of enantioselective reactions and the creation of chiral molecules with potential therapeutic applications.

Upstream product

• 97364-56-2 (1S,2R)-1-Methoxycarbonylamino-2-phenyl-cyclopropanecarboxylic acid 
• 1214-54-6 5-benzylidene Meldrum's acid 
• 3709-32-8 6,6-dimethyl-1-phenyl-5,7-dioxaspiro[2.5]octane-4,8-dione 
• 97364-47-1 (1R,2R)-1-Carbamoyl-2-phenyl-cyclopropanecarboxylic acid 
• 4525-04-6 (E)-(1,5-diphenyl)-7-oxo-6-oxa-4-azaspiro<2.4>hept-4-ene 
• 15732-43-1 (E)-2-phenyl-4-benzylidene-5(4H)-oxazolone 
• 1666-17-7 (E)-N′-benzylidene-4-methylbenzenesulfonohydrazide 
• 4525-04-6 (Z)-(1,5-diphenyl)-7-oxo-6-oxa-4-azaspiro<2.4>hept-4-ene 
• 17606-70-1 (4Z)-4-benzylidene-2-phenyl-1,3-oxazol-5(4H)-one 
• 669058-56-4 ethyl 1-amino-2-phenyl-1-cyclopropanecarboxylate 
• 138770-18-0 (1S,2R)-2-Phenyl-cyclopropane-1,1-dicarboxylic acid ((R)-4,4-dimethyl-2-oxo-tetrahydro-furan-3-yl) ester 
• 180322-86-5 (1R,2R)-1-tert-Butoxycarbonylamino-2-phenyl-cyclopropanecarboxylic acid 
• 27992-27-4 sodium 2-benzylidene-1-tosylhydrazin-1-ide 
• 123039-88-3 methyl cis-1-amino-2-phenylcyclopropanecarboxylate 

Relevant academic research and scientific papers

Expanding the scope of donor/acceptor carbenes to N -phthalimido donor groups: Diastereoselective synthesis of 1-cyclopropane α-amino acids

Warming of 4-phthalimido-N-mesyl-1,2,3-triazole in the presence of alkenes followed by silica gel induced hydrolysis results in a highly diastereoselective and catalyst-free entry to N-phthalimidocyclopropanecarboxaldehydes.

Stereoselective synthesis of 1-aminocyclopropanecarboxylic acid derivatives via ylide cyclopropanation of dehydroamino acid derivatives

1-Aminocyclopropanecarboxylic acid derivatives are synthesized from readily available dehydroamino acid derivatives via sulfur ylide. A range of different ylides are employed and the corresponding aminocyclopropanes are afforded with reasonable diastereoselection in good yields.

PEPTIDYL NITRILES AND USE THEREOF AS DIPEPTIDYL PEPTIDASE I INHIBITORS

The present invention provides compounds of formula (I) in which n, y, X1, X2, A, B, R1, R2, R3, R4 and R5 are as defined in the specification, a process for their preparation, pharmaceutical compositions containing them and their use as dipeptidyl peptidase I (DPPI) inhibitors.

Diastereoselective Synthesis of Cyclopropane Amino Acids Using Diazo Compounds Generated in Situ

A simple and high-yielding method for the preparation of cyclopropane amino acids is described. The novel method involves the one-pot cyclopropanation of readily available dehydroamino acids using aryl and unsaturated diazo compounds generated in situ fro

Application of chiral sulfides to catalytic asymmetric aziridination and cyclopropanation with in situ generation of the diazo compound

Imines and alkenes can be converted into the corresponding aziridines and cyclopropanes (see scheme, PTC = phase-transfer catalyst, Ts = toluene-4-sulfonyl) in good yield with moderate to high d.r. and high ee values using tosylhydrazone salts with catalytic quantities of chiral sulfide (5-20 mol%) and metal catalyst (1 mol%). The process is particularly suited to the synthesis of conformationally locked cyclopropyl amino acids, which can now be prepared in only three steps from commercially available material in 100% ee.

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

α-Hydroxy esters as chiral auxiliaries in asymmetric cyclopropanations by rhodium(II)-stabilized vinylcarbenoids

The use of several α-hydroxy esters as chiral auxiliaries for asymmetric cyclopropanation with rhodium-(II)-stabilized vinylcarbenoids is presented. Use of either (R)-pantolactone or (S)-lactate allowed entry into both series of enantiomeric vinylcyclopropanes with predictable absolute stereochemistry. Steric and electronic modifications of the chiral auxiliary as well as catalyst structure were shown to have major effects on the asymmetric induction. These results were rationalized on the basis of an interaction between the carbonyl oxygen of the chiral auxiliary and the carbenoid carbon. By combining the asymmetric cyclopropanation with a subsequent Cope rearrangement, an enantioselective entry into hydroazulenes was achieved. The potential of the asymmetric cyclopropanation was illustrated by a short synthesis of (1R,2R)-2-phenylcyclopropane amino acid 5.

α-Hydroxy esters as inexpensive chiral auxiliaries in rhodium(II)-catalyzed cyclopropanations with vinyldiazomethanes

High levels of asymmetric induction were achieved in rhodium(II) catalyzed cyclopropanations with chiral vinyldiazomethanes. (R)-(-)-Pantolactone is the most effective chiral auxiliary, but other α-hydroxy esters also give reasonable levels of diastereose

SYNTHESIS OF E AND Z 1-AMINO-2-ARYL(ALKYL)-CYCLOPROPANECARBOXYLIC ACID via MELDRUM DERIVATIVES

The reaction of 5-arylidene(alkylidene)-2,2-dimethyl-1,3-dioxane-4,6-diones (1) (Meldrum's acid derivatives) with dimethylsulfoxonium methylide gave 1-aryl(alkyl)-6,6-dimethyl-4,8-dioxo-5,7-dioxaspiro octanes (2) which , on treatment with sodium meth