Trichlorosilane → 2-Diphenylphosphino-2'-hydroxy-5,5',6,6',7,7',8,8'-octahydro-1,1'-binaphthyl

HRID 260997Notes

Reaction equation

HRID 260997 reaction equation
[PH2:1]([C:3]1[CH:12]=[CH:11][C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]=1[C:13]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH:16]=[CH:15][C:14]=1[O:23]S(C(F)(F)F)(=O)=O)=O.Cl[SiH](Cl)Cl>C(N(CC)CC)C>[C:3]1([P:1]([C:13]2[CH:22]=[CH:17][CH:16]=[CH:15][CH:14]=2)[C:3]2[CH:12]=[CH:11][C:10]3[CH2:9][CH2:8][CH2:7][CH2:6][C:5]=3[C:4]=2[C:13]2[C:22]3[CH2:21][CH2:20][CH2:19][CH2:18][C:17]=3[CH:16]=[CH:15][C:14]=2[OH:23])[CH:12]=[CH:11][CH:10]=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 24811TrichlorosilaneHCID 178527012HCID 178527012, compound

Product 1

HCID 224007882-Diphenylphosphino-2'-hydroxy-5,5',6,6',7,7',8,8'-octahydro-1,1'-binaphthyl

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

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).

Sources & evidence

ORD record
ord-4cb5e974bdbe4143ad2a52e3f64a15a5
Source dataset
uspto-grants-1996_06
Patent number
US05530150

Reaction notes

Loading…