90687-82-4Relevant articles and documents
New functional chiral P-based ligands and application in ruthenium-catalyzed enantioselective transfer hydrogenation of ketones
Meri?, Nermin,Kayan, Cezmi,Gürbüz, Nevin,Karakaplan, Mehmet,Binbay, Nil Ertekin,Aydemir, Murat
, p. 1739 - 1749 (2017/10/26)
Metal-catalyzed asymmetric transfer hydrogenation is a powerful and practical method for the reduction of ketones to produce the corresponding secondary alcohols, which are valuable building blocks in the pharmaceutical, perfume, and agrochemical industries. Hence, a series of novel chiral β-amino alcohols were synthesized by chiral amines with regioselective ring opening of (S)-propylene oxide or reaction with (S)-(+)-2-hydroxypropyl p-toluenesulfonate by a straightforward method. The chiral ruthenium catalytic systems generated from [Ru(arene)(μ-Cl)Cl]2 complexes and chiral phosphinite ligands based on amino alcohol derivatives were employed in asymmetric transfer hydrogenation of ketones to give the corresponding optically active alcohols; (2S)-1-{[(2S)-2-[(diphenylphosphanyl)oxy]propyl][(1R)-1-phenylethyl]amino}propan-2-yldiphenylphosphinitobis[dichol-oro(η6-benzene)ruthenium(II)] acts an excellent catalyst in the reduction of α-naphthyl methyl ketone, giving the corresponding alcohol with up to 99% ee. The substituents on the backbone of the ligands were found to have a remarkable effect on both the conversion and enantioselectivity of the catalysts. Furthermore, this transfer hydrogenation is characterized by low reversibility under these conditions.
Synthesis of β-amino alcohols via the reduction of lactamides derived from ethyl (2S)-lactate with borane-methyl sulfide
Lewis, Frank W.,Eichler, Matthias C.,Grayson, David H.
experimental part, p. 1923 - 1928 (2009/12/29)
Reactions of ethyl (2S)-lactate with various amines affords lactamides that are reduced with borane-methyl sulfide in the presence of boron trifluoride etherate to generate enantiomerically pure β-amino alcohols in good yield. Georg Thieme Verlag Stuttgart.
Stereochemical Structure-Activity Relationship of N-(2,3-Epoxypropyl)-N-(&α-methylbenzyl)benzenesulfonamide Derivatives
Yoneyama, Koichi,Ichizen, Nobumasa,Konnai, Makoto,Takematsu, Tetsuo,Ushinohama, Kazuyuki,Jikihara, Tetsuo
, p. 995 - 1000 (2007/10/02)
The absolute configuration of two assymetric centers in four stereoisomers of N-(2,3-epoxypropyl)-N-(α-methylbenzyl)benzenesulfonamide were determined and their biological activities were tested.Consequently, N--N-benzenesulfonamide was found to be the most active isomer and the stereochemistry of the benzyl position was found to be more important than that of C2 in the epoxypropyl group for biological activity.
