209850-75-9Relevant academic research and scientific papers
Absolute control of helicity at the C-termini in quinoline oligoamide foldamers by chiral oxazolylaniline moieties
Zheng, Dan,Yu, Chengyuan,Zheng, Lu,Zhan, Yulin,Jiang, Hua
supporting information, p. 673 - 676 (2019/08/30)
Absolute one-handed chiral quinoline tetramers andoctamers containing different oxazolylanilines at the C-terminus have been synthesized. The absolute one-handed sense and diastereomeric excess values were valued by 1H NMR. X-ray crystal diffra
Copper-Mediated Diastereoselective C-H Thiolation of Ferrocenes
Kong, Wei-Jun,Shao, Qian,Li, Ming-Hong,Zhou, Zeng-Le,Xu, Hui,Dai, Hui-Xiong,Yu, Jin-Quan
supporting information, p. 2832 - 2836 (2018/09/13)
The first copper-mediated diastereoselective C-H thiolation of ferrocenes has been developed. A chiral oxazoline directing group with tert-butyl substituent is essential to the high diastereoselectivity ratio and the suppression of overreaction of monothi
Oxazolines as Dual-Function Traceless Chromophores and Chiral Auxiliaries: Enantioselective Photoassisted Synthesis of Polyheterocyclic Ketones
Mukhina, Olga A.,Kutateladze, Andrei G.
supporting information, p. 2110 - 2113 (2016/03/05)
2-(o-Amidophenyl)oxa- and -thiazolines undergo excited-state intramolecular proton transfer (ESIPT), generating aza-o-xylylenes capable of intramolecular [4+2] and [4+4] cycloadditions with tethered unsaturated pendants. Facile hydrolysis of the primary p
Palladium-Catalyzed C-2 C-H Heteroarylation of Chiral Oxazolines: Diverse Synthesis of Chiral Oxazoline Ligands
Xi, Tuo,Mei, Yuncai,Lu, Zhan
supporting information, p. 5939 - 5941 (2016/01/09)
A direct, efficient, and practical protocol to install a chiral oxazoline unit onto aryl/heteroaryl rings via palladium-catalyzed C-H functionalization of 2-positions of oxazolines with a variety of halides using dppe as the ligand has been developed. Var
Cooperative thiourea-Bronsted acid organocatalysis: Enantioselective cyanosilylation of aldehydes with TMSCN
Zhang, Zhiguo,Lippert, Katharina M.,Hausmann, Heike,Kotke, Mike,Schreiner, Peter R.
experimental part, p. 9764 - 9776 (2012/01/03)
We report a new thiourea - Bronsted acid cooperative catalytic system for the enantioselective cyanosilylation of aldehydes with yields up to 90% and enantioselectivities up to 88%. The addition of an achiral acid was found to be crucial for high asymmetric induction. Mechanistic investigations using a combination of NMR, ESI-MS, and density functional theory computations (including solvent corrections) at the M06/6-31G(d,p) level of theory suggest that the key catalytic species results from the cooperative interaction of bifunctional thioureas and an achiral acid that form well-defined chiral hydrogen-bonding environments.
Chiral primary amine catalyzed asymmetric epoxidation of α-substituted acroleins
Li, Jiuyuan,Fu, Niankai,Zhang, Long,Zhou, Pengxin,Luo, Sanzhong,Cheng, Jin-Pei
experimental part, p. 6840 - 6849 (2011/03/19)
1,1-Disubstituted terminal alkenes remain challenging substrates in asymmetric epoxidation reactions. In this study, chiral primary amines are shown to catalyze the asymmetric epoxidation of α-substituted acroleins, a versatile type of 1,1-disubstituted t
The synthesis of new oxazoline-containing bifunctional catalysts and their application in the addition of diethylzinc to aldehydes
Coeffard, Vincent,Mueller-Bunz, Helge,Guiry, Patrick J.
experimental part, p. 1723 - 1734 (2009/06/27)
The straightforward preparation of new modular oxazoline-containing bifunctional catalysts is reported employing a microwave-assisted Buchwald-Hartwig aryl amination as the key step. Covalent attachment of 2-(o-aminophenyl)oxazolines and pyridine derivati
New thiazoline-oxazoline ligands and their application in the asymmetric friedel-crafts reaction
McKeon, Sean C.,Mueller-Bunz, Helge,Guiry, Patrick J.
body text, p. 4833 - 4841 (2010/02/28)
Six members of a novel non-C2-symmetric ligand class incorporating an oxazoline and. thiazoline unit have been prepared in a four-step, high-yielding and. convergent: synthesis, in which the key step is a microwave-assisted palladium-catalyzed
Synthesis of non-symmetric bis(oxazoline)-containing ligands and their application in the catalytic enantioselective Nozaki-Hiyama-Kishi allylation of benzaldehyde
Hargaden, Grainne C.,O'Sullivan, Timothy P.,Guiry, Patrick J.
scheme or table, p. 562 - 566 (2008/10/09)
We report the good to high-yielding three-step synthesis of non-symmetrical bis(oxazoline)-containing ligands possessing an N-thienylaniline unit. The convergent synthesis employed a palladium-catalysed aryl amination of 2-(2′-bromothiophene)nitrile as th
Coupling of bulky, electron-deficient partners in aryl amination in the preparation of tridentate bis(oxazoline) ligands for asymmetric catalysis
McManus, Helen A.,Guiry, Patrick J.
, p. 8566 - 8573 (2007/10/03)
A new class of tridentate bis(oxazoline) ligands 7, in which an N-phenylaniline unit links the two oxazoline rings, has been prepared. The key step in their synthesis is a Hartwig-Buchwald type Pd-catalyzed aryl amination between the two bulky o-substituted coupling partners, 2-(2′-bromophenyl)oxazolines 8 and 2-(o-aminophenyl)oxazolines 9. By varying the substituent on the coupling partners, a range of 10 ligands has been prepared in good yield. During the synthesis of 2-(o-aminophenyl)oxazolines 9a-d, a number of products of unexpected side reactions were isolated in two of the three steps. Alternatively, the required 2-(o-aminophenyl)oxazolines 9 were obtained by a DAST-promoted cyclodehydration of hydroxyamides 12a-d without formation of any byproducts.
