90687-83-5Relevant academic research and scientific papers
Catalytic asymmetric transfer hydrogenation of ketones using [Ru(p-cymene)Cl2]2 with chiral amino alcohol ligands
Deshpande, Sudhindra H.,Kelkar, Ashutosh A.,Gonnade, Rajesh G.,Shingote, Savita K.,Chaudhari, Raghunath V.
experimental part, p. 231 - 238 (2011/01/12)
Catalytic asymmetric transfer hydrogenation of aromatic alkyl ketones has been investigated using [Ru(p-cymene)Cl2]2 and new derivatives of β-amino alcohols synthesized from (S)-(-)-lactic acid and mandelic acid as ligands. Chiral secondary alcohols were obtained with good to excellent conversion (60-90%) and moderate to good enantioselectivities (40-86%).
Pyridine-containing chiral macrocycles for the enantioselective recognition of amino acid derivatives and their molecular dynamics simulations
Turgut, Yilmaz,Kocakaya, Safak Ozhan
experimental part, p. 990 - 996 (2010/08/22)
Two novel C2-symmetric optically active pyridine-15-crown-5 type ligands containing lipophilic chains at the stereogenic centres, macrocycles 5 and 6, were prepared from (S)-1,2-propanediol and (S)-3-aryloxy-1,2-propanediol for the enantiomeric recognition of amino acid ester derivatives. These novel macrocycles have been shown to be strong complexing agents for primary organic ammonium salts (with K values of up to 1363.5 M-1, ΔG o of up to 17.86 kJ mol-1 and a selectivity ratio of 80:20) by 1H NMR titration method. These macrocyclic host exhibited enantioselective binding towards the l-enantiomer of phenylalanine methyl ester hydrochloride with KL/KD up to 8.57 in CDCl3 containing 0.25% CD3OD. Experimental results have been detailed with molecular dynamic calculations at atomic level concerning the molecular recognition and discrimination properties of a chiral pyridino-15-crown-5. The binding free energies were calculated as ～-25 kJ mol-1. The results indicated that the host binds and discriminates valine salts better than phenylalanine salts. The molecular dynamics, MM/PBSA calculations are consistent with the 1H NMR results.
Synthesis of C2-symmetric chiral amino alcohols: Their usage as organocatalysts for enantioselective opening of epoxide ring
Turgut, Yilmaz,Aral, Tarik,Karakaplan, Mehmet,Deniz, Pinar,Hosgoren, Halil
experimental part, p. 3365 - 3377 (2011/01/04)
A series of -amino alcohols derivatives were synthesized from (R)-2-amino-1-butanol and (S)-1,2-propanediol, and they have been used as organocatalaysts in the racemic ring opening of epoxide in good yields with high enantiomeric excess (up to 97%). Copyright
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.
Synthesis of novel C2-symmetric chiral crown ethers and investigation of their enantiomeric recognition properties
Turgut, Yilmaz,Aral, Tarik,Hosgoren, Halil
experimental part, p. 2293 - 2298 (2010/03/24)
A series of new C2-symmetric chiral aza crown ether macrocycles 1-4 have been synthesized from (S)-3-aryloxy-1,2-propanediol and (S)-1,2-propanediol for the enantiomeric recognition of amino acid ester derivatives. These new macrocycles have be
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.
