Binap, (A+-)- → (5-[(1,1-Dimethylethyl)thio]-4-[(phenylmethyl)oxy]-2-pyridinyl}methyl acetate

Participants

Reaction Conditions

Reaction Steps

To a solution of (4-[(phenylmethyl)oxy]-5-{[(trifluoromethyl)sulfonyl]oxy}-2-pyridinyl)methyl acetate (12.15 g, 30 mmol) in toluene (500 ml) was added (R)-(+)-2,2′-bis(diphenylphosphino)-1,1′-binaphthyl (1.87 g, 3 mmol). The reaction mixture was purged with argon. Palladium acetate (663 mg, 3 mmol) was added and the mixture was stirred for 10 minutes. 2-Methyl-2-propanethiol sodium salt (4.69, 41.8 mmol) was added and the reaction mixture was flushed again with argon then heated to 80° C. for 7 hours then cooled. The solvent was evaporated. The residue was partitioned between a 1:1 mixture of water and EtOAc. The organic layer was separated and washed with brine, dried over magnesium sulphate and filtered through Kieselguhr. The residue was chromatographed eluting with s 4:1 mixture of hexane:EtOAc affording the product (8.3 g, 80%).

Provenance & Evidence