DIPAMP

• (R, R ) - (- ) -1,2- ethanediylbis [ (o- methoxyphenyl) phenylphosphine ]
• (S, S ) - ( ) -1,2- ethanediylbis [ (o- methoxyphenyl) phenylphosphine ]
• (1R, 2R) -bis [(2- methoxyphenyl) phenylphosphino ] ethane
• (1S, 2S) -bis [(2- methoxyphenyl) phenylphosphino ] ethane

• 55739-58-7 [ (R, R ) enantiomer ]
• 97858-62-3 [ (S, S ) enantiomer ]

Light beige solid

Fixed

102-104 ° C

Attention

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DIPAMP, more precisely each of the two mutually mirror image (S, S ) - and ( R, R) -enantiomer, a chiral bidentate chelate ligand. It belongs to the group of the bidentate chiral phosphine ligands.

Properties

There are three DIPAMP stereoisomers ( S, S) - and (R, R)- DIPAMP chiral molecules with C2 symmetry. Cs - symmetric meso- form ( R, S) is achiral.

The chiral centers are formed by the phosphorus atoms. The rotation of a solution of one gram of (R, R)- DIPAMP in 100 ml of chloroform at 20 ° C is -85 ° at a wavelength of 589 nm

In complexes DIPAMP coordinated with two phosphorus atoms at the metal center. It differs from other chiral phosphine ligands in that the stereocenters complex directly on the metal, and not present in the backbone of the ligands such as DIOP in or chiraphos.

Use

(S, S) - or (R, R)- DIPAMP is used as a chiral phosphine ligand in transition-metal- mediated enantioselective catalysis and results in very high enantiomeric excesses.

The first industrial enantioselective syntheses of pharmaceutically important L- DOPA used enantiopure DIPAMP.