23439-91-0Relevant academic research and scientific papers
Rhodium(I)-, iridium(I)-, and ruthenium(II)-catalyzed asymmetric transfer hydrogenation of ketones using diferrocenyl dichalcogenides as chiral ligands
Nishibayashi, Yoshiaki,Singh, Jai Deo,Arikawa, Yasuyoshi,Uemura, Sakae,Hidai, Masanobu
, p. 13 - 18 (1997)
[R,S;R,S]-Bis[2-[1-(dimethylamino)ethyl]ferrocenyl] dichalcogenides, (R,S)-{[EC5H3CHMe(NMe2)]Fe(C5H5)}2 (E = S, Se, Te), act as chiral ligands for Rh(I)-catalyzed asymmetric transfer hydrog
Potassium 9-O-(1,2:5,6-Di-O-isopropylidene-α-D-glucofuranosyl)-9-boratabicyclononane. A New, Effective Chiral Borohydride Reagent
Brown, Herbert C.,Park, Won Suh,Cho, Byung Tae
, p. 1934 - 1936 (1986)
A convenient and simple synthesis of a new chiral borohydride reagent, potassium 9-O-(1,2:5,6-di-O-isopropylidene-α-D-glucofuranosyl)-9-boratabicyclononane, consisting of a single reducing species, is described.The new reagent is generally effectiv
Manganese catalyzed asymmetric transfer hydrogenation of ketones
Zhang, Guang-Ya,Ruan, Sun-Hong,Li, Yan-Yun,Gao, Jing-Xing
supporting information, p. 1415 - 1418 (2020/11/20)
The asymmetric transfer hydrogenation (ATH) of a wide range of ketones catalyzed by manganese complex as well as chiral PxNy-type ligand under mild conditions was investigated. Using 2-propanol as hydrogen source, various ketones could be enantioselectively hydrogenated by combining cheap, readily available [MnBr(CO)5] with chiral, 22-membered macrocyclic ligand (R,R,R',R')-CyP2N4 (L5) with 2 mol% of catalyst loading, affording highly valuable chiral alcohols with up to 95% ee.
Manganese(I)-Catalyzed H-P Bond Activation via Metal-Ligand Cooperation
Pérez, Juana M.,Postolache, Roxana,Casti?eira Reis, Marta,Sinnema, Esther G.,Vargová, Denisa,De Vries, Folkert,Otten, Edwin,Ge, Luo,Harutyunyan, Syuzanna R.
supporting information, p. 20071 - 20076 (2021/12/03)
Here we report that chiral Mn(I) complexes are capable of H-P bond activation. This activation mode enables a general method for the hydrophosphination of internal and terminal α,β-unsaturated nitriles. Metal-ligand cooperation, a strategy previously not considered for catalytic H-P bond activation, is at the base of the mechanistic action of the Mn(I)-based catalyst. Our computational studies support a stepwise mechanism for the hydrophosphination and provide insight into the origin of the enantioselectivity.
PQXdpap: Helical Poly(quinoxaline-2,3-diyl)s Bearing 4-(Dipropylamino)pyridin-3-yl Pendants as Chirality-Switchable Nucleophilic Catalysts for the Kinetic Resolution of Secondary Alcohols
Murakami, Ryo,Suginome, Michinori,Yamamoto, Takeshi
supporting information, p. 8711 - 8716 (2021/11/24)
Helically chiral poly(quinoxaline-2,3-diyl)s bearing 4-(dipropylamino)pyridin-3-yl pendants at the 5-position of the quinoxaline ring (PQXdpap) exhibited high catalytic activities and moderate to high selectivities (up to s = 87) in the acylative kinetic resolution of secondary alcohols. The solvent-dependent helical chirality switching of PQXdpap between pure toluene and a 1:1 mixture of toluene and 1,1,2-trichloroethane enabled the preparation of either compound of a pair of enantiomerically pure alcohols (>99% ee) from a single catalyst.
Asymmetric transfer hydrogenation of ketones promoted by manganese(I) pre-catalysts supported by bidentate aminophosphines
Azouzi, Karim,Bruneau-Voisine, Antoine,Vendier, Laure,Sortais, Jean-Baptiste,Bastin, Stéphanie
, (2020/05/19)
A series of commercially available chiral amino-phosphines, in combination with Mn(CO)5Br, has been evaluated for the asymmetric reduction of ketones, using isopropanol as hydrogen source. With the most selective ligand, the corresponding manga
RETRACTED ARTICLE: The Manganese(I)-Catalyzed Asymmetric Transfer Hydrogenation of Ketones: Disclosing the Macrocylic Privilege
Passera, Alessandro,Mezzetti, Antonio
supporting information, p. 187 - 191 (2019/12/11)
The bis(carbonyl) manganese(I) complex [Mn(CO)2(1)]Br (2) with a chiral (NH)2P2 macrocyclic ligand (1) catalyzes the asymmetric transfer hydrogenation of polar double bonds with 2-propanol as the hydrogen source. Ketones (43 substrates) are reduced to alcohols in high yields (up to >99 %) and with excellent enantioselectivities (90–99 % ee). A stereochemical model based on attractive CH–π interactions is proposed.
Chiral phosphoric acid catalyzed asymmetric transfer hydrogenation of bulky aryl ketones with ammonia borane
Zhou, Qiwen,Meng, Wei,Feng, Xiangqing,Du, Haifeng,Yang, Jing
supporting information, (2019/11/28)
An asymmetric transfer hydrogenation of bulky aryl ketones with ammonia borane was successfully realized with chiral phosphoric acid (CPA) as catalyst and water as additive. A variety of optically active secondary alcohols were obtained in good to high yi
Direct Asymmetric Hydrogenation and Dynamic Kinetic Resolution of Aryl Ketones Catalyzed by an Iridium-NHC Exhibiting High Enantio- and Diastereoselectivity
Ayya Swamy P, Chinna,Varenikov, Andrii,de Ruiter, Graham
supporting information, p. 2333 - 2337 (2020/02/11)
A chiral iridium carbene-oxazoline catalyst is reported that is able to directly and efficiently hydrogenate a wide variety of ketones in excellent yields and good enantioselectivity (up to 93 % ee). Moreover, when using racemic α-substituted ketones, excellent diastereoselectivities were obtained (dr 99:1) by dynamic kinetic resolution of the in situ formed enolate. Overall, the herein described hydrogenation occurs under ambient conditions using low hydrogen pressures, providing a direct and atom efficient method towards chiral secondary alcohols.
Manganese-Catalyzed Enantioselective Hydrogenation of Simple Ketones Using an Imidazole-Based Chiral PNN Tridentate Ligand
Chen, Jiachen,Hou, Huacui,Ling, Fei,Nian, Sanfei,Wu, Feifei,Xu, Min,Yi, Xiao,Zhong, Weihui
supporting information, p. 285 - 289 (2020/02/18)
A series of Mn(I) catalysts containing imidazole-based chiral PNN tridentate ligands with controllable 'side arm' groups have been established, enabling the inexpensive base-promoted asymmetric hydrogenation of simple ketones with outstanding activities (up to 8200 TON) and good enantioselectivities (up to 88.5percent ee). This protocol features wide substrate scope and functional group tolerance, thereby providing easy access to a key intermediate of crizotinib.
