497262-01-8

Upstream product

• 110-87-2 3,4-dihydro-2H-pyran 
• 497262-00-7 [(1R,2R,3S)-2-(bromomethyl)-3-(hydroxymethyl)-2,3-dimethylcyclopentyl]methyl-4-methylbenzene sulfonate 
• 24057-28-1 pyridinium p-toluenesulfonate 
• 497261-99-1 (1R,2R,3S)-(2-bromomethyl-3-hydroxymethyl-2,3-dimethylcyclopentyl)methanol 
• 497261-97-9 (1R,8R)-8-(bromomethyl)-1,8-dimethyl-3-oxabicyclo[3.2.1]octane-2,4-dione 
• 497261-98-0 (1R,5R,8R)-8-(bromomethyl)-1,8-dimethyl-3-oxabicyclo[3.2.1]octane-2-one 
• 10293-09-1 (1R,4R,7R)-9-bromocamphor 
• 497261-96-8 (1R,7R)-7-(bromomethyl)-1,7-dimethylbicyclo[2.2.1]heptane-2,3-dione 

Downstream Products

• 1027594-31-5 2-{(1R,2R,3S)-2,3-Bis-[(diphenylphosphanyl)-methyl]-1,2-dimethyl-cyclopentylmethoxy}-tetrahydro-pyran 
• 497262-02-9 [(1R,2R,3S)-21,2-dimethyl-2,3-bis(diphenylphosphine-methyl)cyclopentyl]methanol 

Relevant academic research and scientific papers

CHIRAL INTERMEDIATES USEFUL FOR THE PREPARATION OF HYDROXYPHOSPHINE LIGANDS

A compound of formula (I), wherein R1 is hydrogen or a hydroxyl protecting group; and R2 and R3 are same or different and are independently selected from halogen or —O—SO2—X; wherein X is —C1-C4 alkyl; C1-C4 alkyl substituted with one or more halogen; or substituted or unsubstituted phenyl wherein said phenyl substituent is selected from halogen, nitro and C1-C4 alkyl; provided that when R3 is bromine, X is not p-toluoyl; and a process for the preparation thereof.

HYDROXY DIPHOSPHINES AND THEIR USE IN CATALYSIS

The invention relates to novel asymmetrical, chiral hydroxy diphosphines and to derivatives of general formula (I), in addition to their use as catalysts, in particular for enantioselective syntheses.

A new hydroxydiphosphine as a ligand for Rh(I)-catalyzed enantioselective hydrogenation

A new diphosphine ligand bearing a hydroxy group in the backbone was synthesized starting from 9-bromocamphor. The rhodium(I) complex based on this ligand was tested in the hydrogenation of α- and β-amino acid precursors. The activity and selectivity of the catalyst were found to be strongly dependent upon the nature of the substrate. Thus, β-acetylamino carboxylates were obtained with up to 97% ee.