474093-57-7

Upstream product

• 226393-36-8 1-(N,N-dimethylamino)-1-r-oxo-2-t,5-t-diphenylphospholane 
• 226393-31-3 1-(N,N-dimethylamino)-1-r-oxo-2-t,5-t-diphenylphosphol-3-ene 
• 474049-73-5 (S,S)-(-)-1-hydroxy-1-oxo-2,5-trans-diphenylphospholane 
• 886-65-7 trans,trans-1,4-Diphenyl-1,3-butadiene 
• 474093-56-6 (S,S)-(-)-1-chloro-1-r-oxo-2-c,5-t-diphenylphospholane 

Downstream Products

• 882354-12-3 (2S,5S)-(-)-1-(1-naphthyl)-1-oxo-2,5-diphenylphospholane 
• 882353-88-0 (2S,5S)-(-)-1-(3,5-dimethylphenyl)-1-oxo-2,5-diphenylphospholane 
• 934421-88-2 (S,S)-1-chloro-2,5-trans-diphenylphospholane 
• 949575-78-4 (2S,5S)-(+)-6-(tert-butoxypyrid-2-yl)-2,5-diphenylphospholane 
• 1372716-19-2 di-tert-butyl bis((2S,5S)-1-oxo-2,5-diphenyl-λ5-phospholan-1-yl)pyrazine-1,4-dicarboxylate 
• 1372716-17-0 7-((2S,5S)-1-oxo-2,5-diphenyl-λ5-phospholan-1-yl)-2,3,4,5-tetrahydro-azepine-1-carboxylic acid methyl ester 
• 1372716-15-8 1-(methoxycarbonyl)-6-((2S,5S)-1-oxo-2,5-diphenyl-λ5-phospholan-1-yl)-3,4-dihydro-2H-pyridine 
• 1372716-16-9 6-((2S,5S)-1-oxo-2,5-diphenyl-λ5-phospholan-1-yl)-3,4-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester 
• 1372716-18-1 7-((2S,5S)-1-oxo-2,5-diphenyl-λ5-phospholan-1-yl)-2,3,4,5-tetrahydro-azepine-1-carboxylic acid tert-butyl ester 
• 138258-77-2 (S,S)-(-)-1-r,2-c,5-t-triphenylphospholane 

Relevant academic research and scientific papers

Enantioselective Synthesis of Atropisomeric Biaryls using Biaryl 2,5-Diphenylphospholanes as Ligands for Palladium-Catalysed Suzuki-Miyaura Reactions

Here we describe the development of biaryl 2,5-diphenylphospholanes as a new class of C2-symmetric, monodentate ligands for asymmetric Suzuki-Miyaura (ASM) reactions. Screening of a series of exemplary phospholanes led to the identification of two ligands that were used to prepare a range of atropisomeric biaryl and heterobiaryl products with good to excellent levels of enantioselectivity (up to 97:3 e.r.) under mild conditions. DFT studies suggest that the formation of a constraining ligand pocket and coordination of one of the biaryl methoxy groups in the optimised ligands to the metal centre is crucial for restricting conformational freedom in the bond-forming step. (Figure presented.).

Bis-(2,5-diphenylphospholanes) with sp2 carbon linkers: Synthesis and application in asymmetric hydrogenation

(Chemical Equation Presented) Four chiral diphosphine ligands consisting of bis(2,5-diphenylphospholan-1-yl) groups connected by the sp2 carbon linkers 2,3-quinoxaline ((S,S)-Ph-Quinox), 2,3-pyrazine ((S,S)-Ph-Pyrazine), maleic anhydride ((S,S)-Ph-MalPhos), and 1,1′-ferrocene ((S,S)-Ph-5-Fc) were synthesized, and their cationic [rhodium-(I)(COD)] complexes were prepared. These complexes were tested in asymmetric hydrogenation of functionalized olefins. [((S,S)-Ph-Quinox)Rh(COD)]BF4 showed high activity and selectivity against itaconate and dehydroamino acid substrates. The corresponding (S,S)-Ph-Pyrazine and (S,S)-Ph-MalPhOS complexes exhibited lower activities and selectivities. [((S,S)-Ph-S-Fc)Rh(COD)]BF4 showed high activity with low selectivity for these substrates, but high activity and selectivity against 2-C-substituted cinnamate salts, whereas rhodium complexes of (S,S)-Ph-Quinox and (R,R)-Ph-BPE showed low activity and selectivity against 2-C-substituted cinnamate salts.

Enantioselective hydrogenation with self-assembling rhodium phosphene catalysts: Influence of ligand structure and solvent

Three sets of new and related chiral phospholane and phosphepine ligands have been prepared for Rh-catalyzed enantioselective hydrogenation. The size and substitution pattern of the cyclic monophosphanes were varied. More importantly, the ligands differ in the nature of the heterocyclic group linked to the trivalent phosphorus atom: 2-pyridone or 2-alkoxypyridine. In the corresponding Rh complexes, the pyridone units of two monodentate P ligands can assemble by hydrogen bonding and form chelates. In contrast, synthetic precursors bearing alkoxypyridine appendages are not able to aggregate via intramolecular hydrogen bonds. The nature of self-assembly is dependent on the nature of the P ligand and the solvent used for the hydrogenation (CH 2Cl2 vs. MeOH). These features affect the rate of the reaction as well as the enantioselectivity, which varied in the range of 0-99 % ee Complexation studies and DFT calculations were performed to explain these differences.

BISPHOSPHOLANES FOR USE AS CATALYSTS IN ASYMMETRIC REACTIONS

The invention is a set of novel bisphospholane ligands that can be complexed with transition metals. These complexes are useful as catalysts in asymmetric reactions such as asymmetric hydrogenation.

Synthesis and first applications of a new family of chiral monophosphine ligand: 2,5-diphenylphosphospholanes

The cyclic phosphinic acid 1-hydroxy-1-r-oxo-2c,5-t-diphenylphospholane was synthesized and resolved into enantiomers through fractional crystallization of the quinine salts. The P-phenyl, P-methyl and P-benzyl tertiary phosphine oxides were obtained from