141970-77-6

Basic information

• Product Name: 2-Furanpropanoic acid, a-[[(phenylmethoxy)carbonyl]amino]-, methyl ester, (R)-
• CAS NO: 141970-77-6
• Molecular Formula: C16H17NO5
• Molecular Weight: 303.315
• Mol File: 141970-77-6.mol

Chemical Properties

• CAS DataBase Reference: 2-Furanpropanoic acid, a-[[(phenylmethoxy)carbonyl]amino]-, methyl ester, (R)-(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Furanpropanoic acid, a-[[(phenylmethoxy)carbonyl]amino]-, methyl ester, (R)-(141970-77-6)
• EPA Substance Registry System: 2-Furanpropanoic acid, a-[[(phenylmethoxy)carbonyl]amino]-, methyl ester, (R)-(141970-77-6)

Safety Data

• Hazardous Substances Data: 141970-77-6(Hazardous Substances Data)

Upstream product

• 98-01-1 furfural 
• 620972-00-1 (E)-2-Benzyloxycarbonylamino-3-furan-2-yl-acrylic acid methyl ester 
• 161282-26-4 methyl (Z)-2-<(benzyloxy)carbonylamino>-3-(furan-2-yl)prop-2-enoate 

Downstream Products

• 127759-47-1 methyl (2R)-2-amino-3-(2-furyl)propionate 
• 904682-06-0 methyl (2R)-(-)-2-{[(4-bromophenyl)sulfonyl]amino}-3-(2-furyl)propanoate 
• 904682-07-1 methyl (+)-(2R)-[(4-bromobenzenesulfonyl)-prop-2-ynyl-amino]-3-furan-2-yl-propanoate 

Relevant articles and documents

A Bulky Three-Hindered Quadrant Bisphosphine Ligand: Synthesis and Application in Rhodium-Catalyzed Asymmetric Hydrogenation of Functionalized Alkenes

A bulky three-hindered quadrant bisphosphine ligand, di-1-adamantylphosphino(tert-butylmethylphosphino)methane, named BulkyP*, has been synthesized via a convergent short pathway with chromatography-free procedures. The ligand is a crystalline solid and can be readily handled in air. Its rhodium(I) complex exhibits very high enantioselectivities and catalytic activities in the asymmetric hydrogenation of functionalized alkenes.

METHOD FOR PRODUCING OPTICALLY ACTIVE 1,2-BIS(DIALKYLPHOSPHINO)BENZENE DERIVATIVE

An industrially advantageous method for producing an optically active 1,2-bis(dialkylphosphino)benzene derivative of the present invention is provided. The method is characterized in that a phosphine-borane compound represented by the following general formula (1) is subjected to a deboronation reaction, followed by lithiation, then the reaction product is subjected to reaction with an alkyldihalogenophosphine represented by RaPX′2, and thereafter the reaction product is subjected to reaction with a Grignard reagent represented by RbMgX″ to produce an optically active 1,2-bis(dialkylphosphino)benzene derivative (A). R1 and R2 respectively represent an alkyl group having 1 to 8 carbon atoms, and the number of carbon atoms is different between R1 and R2. Ra is either R1 or R2 and Rb is the other of R1 and R2. X, X′, and X″ each represent a halogen atom.

Three-hindered quadrant phosphine ligands with an aromatic ring backbone for the rhodium-catalyzed asymmetric hydrogenation of functionalized alkenes

The three-hindered quadrant phosphine ligands (R)-1-tert- butylmethylphosphino-2-(di-tert-butylphosphino)benzene ((R)-3H-BenzP*) and (R)-2-tert-butylmethylphosphino-3-(di-tert-butylphosphino)quinoxaline ((R)-3H-QuinoxP*) exhibited good to excellent enantioselectivities in the rhodium-catalyzed asymmetric hydrogenation of selected dehydroamino acid derivatives, enamides, and ethenephosphonates.

Rigid P-chiral phosphine ligands with tert -butylmethylphosphino groups for rhodium-catalyzed asymmetric hydrogenation of functionalized alkenes

Both enantiomers of 2,3-bis(tert-butylmethylphosphino)quinoxaline (QuinoxP*), 1,2-bis(tert-butylmethylphosphino)benzene (BenzP*), and 1,2-bis(tert-butylmethylphosphino)-4,5-(methylenedioxy)benzene (DioxyBenzP*) were prepared in short steps from enantiopure (S)- and (R)-tert-butylmethylphosphine-boranes as the key intermediates. All of these ligands were crystalline solids and were not readily oxidized on exposure to air. Their rhodium complexes exhibited excellent enantioselectivities and high catalytic activities in the asymmetric hydrogenation of functionalized alkenes, such as dehydroamino acid derivatives and enamides. The practical utility of these catalysts was demonstrated by the efficient preparation of several chiral pharmaceutical ingredients having an amino acid or a secondary amine component. A rhodium complex of the structurally simple ligand BenzP* was used for the mechanistic study of asymmetric hydrogenation. Low-temperature NMR studies together with DFT calculations using methyl α-acetamidocinnamate as the standard model substrate revealed new aspects of the reaction pathways and the enantioselection mechanism.

Enantiopure 1,2-Bis(tert-butylmethylphosphino)benzene as a highly efficient ligand in rhodium-catalyzed asymmetric hydrogenation

Figure Presented. An electron-rich P-stereogenic bisphosphine ligand named "BenzP" was conveniently prepared from o-dibromobenzene and enantiopure tert-butylmethylphosphine-borane. Its rhodium complex exhibited excellent enantioselectivities of up to 99.9% and high catalytic activity of up to 10000 h-1 TOF in asymmetric hydrogenations of various functionalized alkenes.

Asymmetric rhodium-catalyzed hydrogenation meets gold-catalyzed cyclization: Enantioselective synthesis of 8-hydroxytetrahydroisoquinolines

Different furyl-substituted (Z)-dehydroamino acid derivatives were hydrogenated with the rhodium/Mandyphos(OMe)-system to give enantiomeric excesses between 80 and 98%. The absolute configuration of the newly formed stereogenic center was determined by an

Synthesis of enantiomerically pure D- and L-(heteroaryl)alanines by asymmetric hydrogenation of (Z)-α-amino-α,β-didehydro esters

Homogeneous asymmetric hydrogenation of a wide range of methyl and tert-butyl (Z)-2-(acylamino)-3-(heteroaryl)acrylates (see 1a-f and 2a-d, f, g, resp.) catalyzed by diphosphinerhodium catalysts was studied for the synthesis of enantiomerically pure 3-fur