Trifluoromethanesulfonamide, diphenylphosphoramide and diphenylthiophosphoramide of (R)-(+)-1,1′-binaphthyl-2,2′-diamine as chiral catalyst ligands for the titanium(IV) alkoxide-promoted addition of diethylzinc to aldehydes

✍ Scribed by Min Shi; Wen-Sheng Sui

• Publisher: John Wiley and Sons
• Year: 2000
• Tongue: English
• Weight: 160 KB
• Volume: 12
• Category: Article
• ISSN: 0899-0042
• DOI: 10.1002/1520-636x(2000)12:7<574::aid-chir5>3.0.co;2-s

✦ Synopsis

Chiral trifluoromethanesulfonamide 4, diphenylphosphoramides 5 and 6, and phenylthiophosphoramide 7 were prepared from the reaction of trifluoromethanesulfonic anhydride, diphenylphosphinic chloride, and diphenylthiophosphinic chloride with (R)-(+)-1,1Ј-binaphthyl-2,2Ј-diamine, respectively. They were used as catalytic chiral ligands in the asymmetric addition reaction of diethylzinc to aldehydes in the presence of titanium(IV) isopropoxide to give the corresponding sec-alcohols with 43-54%, 18-22%, 30-34%, and 52-64% enantiomeric excess, respectively. Chirality 12: 574-580, 2000.