(S)-(+)-1,1'-Bi-2-naphthol bis(trifluoromethanesulfonate) → HCID 178527012, Verbindung

HRID 260996Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 260996
[F:1][C:2]([F:36])([F:35])[S:3]([O:6][C:7]1[CH:16]=[CH:15][C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[C:8]=1[C:17]1[C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[CH:20]=[CH:19][C:18]=1OS(C(F)(F)F)(=O)=O)(=[O:5])=[O:4].[PH3:37]=[O:38]>[Pd]>[PH2:37]([C:18]1[CH:19]=[CH:20][C:21]2[C:26](=[CH:25][CH:24]=[CH:23][CH:22]=2)[C:17]=1[C:8]1[C:9]2[C:14](=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH:15]=[CH:16][C:7]=1[O:6][S:3]([C:2]([F:1])([F:36])[F:35])(=[O:4])=[O:5])=[O:38]

Komponenten

4

Edukt 2

HCID 389883(S)-(+)-1,1'-Bi-2-naphthol bis(trifluoromethanesulfonate)HCID 178527022HCID 178527022, Verbindung

Produkt 1

HCID 178527012HCID 178527012, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 23938PalladiumKatalysator

Versuchsvorschrift

In detail, 2,2'-dihydroxy-5,5',6,6',7,7',8,8'-octahydro-1,1'-binaphthyl (3), which is obtained by hydrogenation of 1,1'-bi-2-naphthol in the presence of a platinum oxide catalyst, is reacted with trifluoromethanesulfonic acid anhydride (4) in accordance with the process described in Tetrahedron Letters, Vol. 31, pp. 6321-6324 (1990) to obtain 2,2'-bis(trifluoromethanesulfonyloxy)-5,5',6,6',7,7',8,8-octahydro-1,1'-binaphthyl (5). Compound (5) is reacted with phosphine oxide (6) in the presence of a palladium catalyst to obtain compound (7). Compound (7) is first reduced by trichlorosilane in the presence of triethylamine and then hydrolyzed or first hydrolyzed and then reduced to obtain 2- diphenylphosphino-2'-hydroxy-5,5',6,6',7,7',8,8'-octahydro-1,1'-binaphthyl (8). Compound (8) is reacted with a chlorophosphite derivative (9) in the presence of triethylamine to obtain an optically active phosphine compound of formula (II).

Quellen und Nachweise

ORD-Eintrag
ord-6f1b3b7169a8495881a605839106ed1f
Quelldatensatz
uspto-grants-1996_06
Patentnummer
US05530150

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