146476-37-1Relevant articles and documents
Novel chiral sulfinamide phosphines: Valuable precursors to chiral β-aminophosphines
Chen, Peng,Su, Xiao,Zhou, Wei,Xiao, Yuanjing,Zhang, Junliang
, p. 2700 - 2706 (2016/05/10)
Starting from commercially available aldehyde and chiral tert-butanesulfinamide, a series of chiral sulfinamide phosphines (Xiao-Phos) were synthesized via a two-step condensation-nucleophilic addition procedure. In most cases, nucleophilic addition of th
Synthesis of iron P-N-P' and P-NH-P asymmetric hydrogenation catalysts
Sonnenberg, Jessica F.,Lough, Alan J.,Morris, Robert H.
, p. 6452 - 6465 (2015/02/19)
Complexes of the type mer,trans-[Fe(P-N-P)(CO)2Br]BF4 are known to be precatalysts for the asymmetric direct hydrogenation of ketones and imines. Employing related ligand scaffolds, we successfully generated and tested the series of three new precatalysts [Fe(PCy2CH2CH-NCH(R)CH2PPh2)(CO)2Br]BF4 with chirality derived from (S)-amino alcohols with phenyl, benzyl, and isopropyl substituents (R), yielding fairly active and selective systems. For the reduction of acetophenone to (S)-1-phenylethanol turnover frequencies up to 920 h-1 and up to 74% enantiomeric excess at 50 °C and 5-25 atm of H2 were obtained. We found, however, that placing these large groups R next to nitrogen was found to be deleterious to catalytic activity. Extending the scope of the ligand structure, we then developed a series of six P-N-P and five P-NH-P systems starting with o-diphenylphosphinobenzaldehyde and the phosphine-amines PPh2CHR1CHR2NH2 (R1 = H, Ph, CH2Ph, iPr with R2 = H or R1 = Me, Ph with R2 = Ph) as well as their corresponding [Fe(P-N-P)(NCMe)3][BF4]2 and [Fe(P-NH-P)(NCMe)3][BF4]2 complexes, which were not catalytically active. Finally, we made the new achiral iron complex mer,cis-Fe(PPh2(o-C6H4)CHNCH2CH2PPh2)(CO)Br2, which was active for the direct hydrogenation of acetophenone, achieving turnover frequencies of 800 h-1 at 50°C and 25 atm of H2.
Synthesis of chiral aminophosphines from chiral aminoalcohols via cyclic sulfamidates
Guo, Rongwei,Lu, Shuiming,Chen, Xuanhua,Tsang, Chi-Wing,Jia, Wenli,Sui-Seng, Christine,Amoroso, Dino,Abdur-Rashid, Kamaluddin
supporting information; experimental part, p. 937 - 940 (2010/05/02)
(Chemical Equation Presented) Protic aminophosphines with multiple chiral centers were synthesized in good yields and high purity by the nucleophilic ring-opening of N-protected cyclic sulfamidates with metal phosphides, followed by hydrolysis and deprote