215317-22-9Relevant academic research and scientific papers
2,5-Dimethyl-3,4-bis[(2R,5R)-2,5-dimethylphospholano]thiophene: First member of the hetero-DuPHOS family
Benincori, Tiziana,Pilati, Tullio,Rizzo, Simona,Sannicolo, Franco,Burk, Mark J.,De Ferra, Lorenzo,Ullucci, Elio,Piccolo, Oreste
, p. 5436 - 5441 (2007/10/03)
The 2,5-dimethyl-3,4-bis[(2R,5R)-2,5-dimethylphospholano]thiophene (UlluPHOS), a new thiophene-based analogue of (R,R)-1,2-bis(phospholano)benzene (Me-DuPHOS), was synthesized, geometrically and electronically characterized, and employed as ligand of Rh and Ru in some standard hydrogenation reactions of prostereogenic functionalized carbon-carbon and carbon-oxygen double bonds. The synthesis of UlluPHOS is much easier than that provided for Me-DuPHOS. UlluPHOS and Me-DuPHOS display very similar geometries, while the electronic availability of the former is higher than that exhibited by the latter. The Rh and Ru complexes of UlluPHOS produced excellent enantiomeric excesses (98.9-99.5%) in the hydrogenation of N-acetyl-α-enamino acids and reaction rates higher than those found when employing the analogous complexes of Me-DuPHOS.
A convergent, scalable synthesis of HIV protease inhibitor PNU-140690
Fors, Kristina S.,Gage, James R.,Heier, Richard F.,Kelly, Robert G.,Perrault, William R.,Wicnienski, Nancy
, p. 7348 - 7356 (2007/10/03)
PNU-140690, an inhibitor of the HIV protease enzyme undergoing clinical evaluation as a chemotherapeutic agent for treatment of AIDS, was synthesized by a convergent approach amenable to large-scale preparation in a pilot plant environment. The key step is the aldol addition of nitroaromatic ester (+)-8 to aldehyde 19e. The two stereocenters present in the target molecule were each set independently by resolution of enantiomers. Intermediates along the synthetic routes were chosen to maximize opportunities for isolation and purification by crystallization.
