103729-97-1Relevant academic research and scientific papers
Preparation of several BINOL-based polymeric ligands for the enantioselective addition of triethylaluminium to aromatic aldehydes
Liu, Dacai,Ouyang, Kunbing,Yang, Nianfa
, p. 1018 - 1023 (2016)
The synthesis of several polystyrene-supported BINOL (1,1-binaphthol) ligands via radical polymerization is described. These BINOL-based polymeric ligands were applied to the enantioselective addition of triethylaluminium to aromatic aldehyde in the presence of titanium isopropoxide. The products were obtained with up to 93% enantiomeric excess (ee) in good to excellent yield. The ligands were easily recovered and reused without losing their catalytic activity as well as enantioselectivity.
([2]Paracyclo[2](5,8)quinolinophan-2-yl)carbinols as catalysts for diethylzinc addition to aldehydes: Cooperative effects of planar and central chirality on the asymmetric induction
Ricci, Giacomo,Ruzziconi, Renzo
, p. 1817 - 1827 (2005)
A systematic study to assess the contribution of planar and central chirality to the asymmetric induction in the diethylzinc addition to aromatic and aliphatic aldehydes has been carried out using planar chiral quinolinophanylcarbinols (Rp)-1 and (Rp)-11 and diastereomeric quinolinophanylcarbinols (Rp,R)- and (R p,S)-5-8, exhibiting both planar and central chirality as catalysts. The stereochemistry of the addition process leading to aryl- or 1-alkylpropanols seems to be mostly controlled by the central chirality. Nevertheless, the planar chirality shows a remarkable cooperative effect on the degree of asymmetric induction, which turns out to be positive or negative depending on the configuration of the stereogenic carbon of the catalyst.
Ketopinic acid derived bis(hydroxy amides) as cheap, chiral ligands for the enantioselective ethylation of aromatic aldehydes
De Las Casas Engel, Tomas,Maroto, Beatriz Lora,De La Moya Cerero, Santiago
, p. 1717 - 1727 (2010)
Readily accessible, C2- and pseudo-C2-symmetric bis(hydroxy amides), derived from, commercially available (+)-ketopinic acid and protic diamines, are promising, cheap, chiral ligands for the synthetically valuable, enantioselective a
Readily available new pyridyl alcohols derived from D-glucose as ligands for the enantioselective addition of diethylzinc to aldehydes
Huang, Hanmin,Zheng, Zhuo,Chen, Huilin,Bai, Changmin,Wang, Junwei
, p. 1285 - 1289 (2003)
A series of new chiral ligands derived from D-glucose has been synthesized and applied in the enantioselective addition of diethylzinc to aldehydes. Up to 94.1% e.e. was obtained in the ethylation reactions. In contrast to the ligands derived from D-fructose, ligands derived from D-glucose gave the opposite asymmetric induction.
Roadmap towards N-heterocyclic [2.2]paracyclophanes and their application in asymmetric catalysis
Busch, Mark,Cayir, Merve,Nieger, Martin,Thiel, Werner R.,Braese, Stefan
, p. 6108 - 6123 (2013)
A novel family of [2.2]paracyclophane derivatives is described. Different substituted pyrazole, triazole and pyrimidine moieties were introduced to the [2.2]paracyclophane scaffold and the products were characterized spectroscopically and by X-ray structu
C2-symmetric N-(β-mercaptoethyl)pyrrolidine as a chiral catalyst ligand in the addition reaction of aldehydes and diethylzinc
Masaki,Satoh,Makihara,Shi
, p. 454 - 456 (1996)
A chiral C2-symmetric N-(β-mercaptoethyl)pyrrolidine bearing 6-membered benzylidene acetal functionalities fused at the 2,3- and 4,5-positions was found to exhibit high efficiency in the asymmetric addition reaction of aldehydes with diethylzin
Highly enantioselective addition of diethylzinc to aldehydes catalyzed by a new chiral C2-symmetric Ti-diol complex
Yang, Xiao-Wu,Shen, Jian-Heng,Da, Chao-Shan,Wang, Heng-Shan,Su, Wu,Liu, Da-Xue,Wang, Rui,Choi, Michael C.K.,Chan, Albert S.C.
, p. 6573 - 6575 (2001)
A novel C2-symmetric chiral diol was synthesized and was found to catalyze the enantioselective addition of diethylzinc to aldehydes to afford optically active secondary alcohols with ee's up to 99%.
The effect of high pressure on the diastereoselectivity of intermolecular all-carbon Diels-Alder reactions
Tietze, Lutz F.,Henrich, Marielouise,Niklaus, Anja,Buback, Michael
, p. 297 - 304 (1999)
The influence of high pressure on the diastereoselectivity of the intermolecular all-carbon Diels-Alder reaction of the phenylbutadienes 1 a- c with the dicyanoethylenes 2a-d to give the cyclohexenes 3-8 is described. The differences in activation volume, ΔΔV(≠), for the two pathways leading to cis and trans diastereomers range from - (0.7 ± 0.8) to - (6.4 ± 0.6) cm3mol-1 indicating a pressure-induced increase of diastereoselectivity in favour of the cis adducts 3a-d, 5a-d and 7b-d.
Synthesis of N-α-pyridylmethyl amino alcohols and application in catalytic asymmetric addition of diethylzinc to aromatic aldehydes
Wu, Yangjie,Yun, Hongying,Wu, Yusheng,Ding, Kuiling,Zhou, Ying
, p. 3543 - 3552 (2000)
A series of novel chiral ligands 2a-2f were conveniently prepared from β-amino alcohols through a two-step reaction and applied to catalyze the enantioselective addition of diethylzinc to benzaldehyde. Among them, ligand 2c was found to show the best asym
Engineering catalysts for enantioselective addition of diethylzinc to aldehydes with racemic amino alcohols: Nonlinear effects in asymmetric deactivation of racemic catalysts
Long, Jiang,Ding, Kuiling
, p. 544 - 547 (2001)
Correct additions make a difference: Asymmetric deactivation and asymmetric amplification concepts coupled with a high-throughput screening technique provided a successful strategy for designing a highly enantioselective catalytic system by simple combination of a racemic amino alcohol (rac-DB) and a nonracemic additive (AA). The example in the scheme shows the conversion of 1 into 2 with up to 92.7% ee.
