A highly stereoselective synthesis of optically active trisubstituted 1,2-ethylenediamines: the first example of grignard addition to N-diphenylphosphinoyl ketimines derived from amino acids.
The efficient synthesis of optically active trisubstituted 1,2-ethylenediamines is described. Addition of aryl and/or alkyl Grignard reagents to alpha-amino N-diphenylphosphinoyl ketimines derived from alpha-amino acids was demonstrated to afford the desired trisubstituted 1,2-ethylenediamines in good yields and with high diastereoselectivities. Subsequent removal of the diphenyphosphinoyl group from the adduct was smoothly accomplished in reasonable yield without racemization under newly developed reductive conditions.
Kohmura
Yoshinori
Y
Process Research, Process R & D, Laboratories for Technology Development, Banyu Pharmaceutical Co. Ltd., 9-1, Kamimutsuna 3-Chome, Okazaki, Aichi 444-0858, Japan. yoshinori_kohmura@merck.com
Mase
Toshiaki
T
D000596:Amino Acids / Q000737:chemistry*; D005029:Ethylenediamines / Q000737:chemistry*; D007097:Imines / Q000737:chemistry*; D015394:Molecular Structure; D013237:Stereoisomerism
D000596:Amino Acids; D005029:Ethylenediamines; D007097:Imines; C031234:ethylenediamine