1,3‐bis[<i>N</i>‐sulfonyl‐(1<i>R</i>,2<i>S</i>)‐1,3‐diphenyl‐2‐aminopropanol]benzene: An excellent ligand for titanium‐catalyzed asymmetric AlPh₃(THF) additions to aldehydes

Abstract

Asymmetric AlPh(3) (THF) additions to a wide variety of aldehydes catalyzed by a titanium catalyst of 20 mol % 1,3-bis[N-sulfonyl-(1R,2S)-1,3-diphenyl-2-aminopropanol]benzene (1) are reported. The catalytic system works excellently for aromatic aldehydes bearing either an electron-donating or an electron-withdrawing substituent on the aromatic ring to afford secondary diaryl alcohols in excellent isolated yields of >or=95% and excellent enantioselectivities of >or=94% ee. The phenyl addition to cinnamaldehyde or 2-furylaldehyde gave corresponding secondary alcohols in 85% and 95% ee, respectively. For aliphatic aldehydes, increasing enantioselectivities of the addition products in terms of increasing steric sizes of aldehydes are observed, and this trend goes from the linear 1-pentanal (87% ee), the secondary cyclohexylaldehyde (95% ee) or the 2-methylpropanal (97% ee), to the tertiary 2,2-dimethylpropanal (99% ee).