DIPAMP

from Wikipedia, the free encyclopedia
Structural formula
Structural formula of (S, S) - and (R, R) -DIPAMP
( S , S ) shape (top) and ( R , R ) shape (bottom)
General
Surname DIPAMP
other names
  • ( R , R ) - (-) - 1,2-Ethanediylbis [( o -methoxyphenyl) phenylphosphine]
  • ( S , S ) - (+) - 1,2-ethanediylbis [( o -methoxyphenyl) phenylphosphine]
  • (1 R , 2 R ) -Bis [(2-methoxyphenyl) phenylphosphino] ethane
  • (1 S , 2 S ) -Bis [(2-methoxyphenyl) phenylphosphino] ethane
Molecular formula C 28 H 28 O 2 P 2
Brief description

light beige solid

External identifiers / databases
CAS number
  • 55739-58-7 [( R , R ) -enantiomer]
  • 97858-62-3 [( S , S ) -enantiomer]
EC number 678-214-4
ECHA InfoCard 100.203.286
PubChem 11419748
ChemSpider 9594634
Wikidata Q411299
properties
Molar mass 458.48 g mol −1
Physical state

firmly

Melting point

102-104 ° C

safety instructions
GHS labeling of hazardous substances
07 - Warning

Caution

H and P phrases H: 315-319-335-413
P: 261-305 + 351 + 338
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

DIPAMP is a chemical compound from the group of phosphines , which is used as a chiral bidentate chelating ligand .

properties

There are three DIPAMP stereoisomers: The ( S , S ) and ( R , R ) -DIPAMP enantiomers are chiral molecules with C 2 symmetry . The C s -symmetric meso -form ( R , S ) is achiral.

Achiral: meso -DIPAMP.

The centers of chirality 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 coordinates with both phosphorus atoms at the metal center. It differs from other chiral phosphine ligands in that the stereocenters complex directly on the metal and are not located in the backbone of the ligands, such as in DIOP or Chiraphos .

use

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

The first industrial enantioselective syntheses of the pharmaceutically important L -DOPA used enantiomerically pure DIPAMP.

Individual evidence

  1. ↑ a b DIPAMP data sheet at Acros, accessed on February 20, 2010.
  2. ↑ a b data sheet (R, R) -DIPAMP from Sigma-Aldrich , accessed on March 24, 2011 ( PDF ).
  3. ^ BD Vineyard, WS Knowles, MJ Sabacky, GL Bachman, D. J. Weinkauff: Asymmetric hydrogenation. Rhodium chiral bisphosphine catalyst. In: Journal of the American Chemical Society , 1977, 99, pp. 5946-5952, doi : 10.1021 / ja00460a018 .
  4. ^ Hans Rudolf Christen, Fritz Vögtle: Organic Chemistry, Volume 2. 2nd Edition. Salle, Frankfurt / Main 1996, ISBN 3-7935-5398-1 .