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

HRID 260994Notes

Reaction equation

HRID 260994 reaction equation
[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]

Participants

4

Reactant 2

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

Product 1

HCID 178527012HCID 178527012, compound

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

More specifically, following Tetrahedron Letters, 31, 6321-6324 (1990), trifluoromethanesulfonic anhydride (4) is reacted with 1,1-bi-2-naphthol (3) to form 2,2'-bis(trifluoromethanesulfonyloxy)-1,1'-binaphthyl (5). This compound (5) is reacted with phosphine oxide (6) in the presence of a palladium catalyst to form 2-phosphinyl-2'-trifluoromethanesulfonyloxy-1,1'-binaphthyl (7). Compound (7) is then reduced in the presence of triethylamine, followed by hydrolysis of the reduction product to form 2-phosphino-2'-hydroxy-1,1'-binaphthyl (8). Further, this compound (8) is reacted with chlorophosphine (9) in the presence of triethylamine, whereby the phosphine compound (I) of the present invention is prepared.

Sources & evidence

ORD record
ord-787b478ab59e4b42899d325320eee26c
Source dataset
uspto-grants-1996_06
Patent number
US05530150

Reaction notes

Loading…