Asymmetric transfer hydrogenation of aromatic ketones with chiral diamino-thiophene/iridium catalyst systems

被引:12
作者
Zhang, Xue-Qin
Li, Yan-Yun
Dong, Zhen-Rong
Shen, Wei-Yi
Cheng, Zhi-Bo
Gao, Jing-Xing [1 ]
机构
[1] Xiamen Univ, State Key Lab Phys Chem Solid Surfaces, Xiamen 361005, Fujian, Peoples R China
基金
中国国家自然科学基金;
关键词
Thiophene ligands; Asymmetric transfer hydrogenation; Aromatic ketone; Chiral alcohols; TRANSITION-METAL-COMPLEXES; COORDINATION CHEMISTRY; RUTHENIUM COMPLEXES; LIGANDS; ALCOHOLS;
D O I
10.1016/j.molcata.2009.03.019
中图分类号
O64 [物理化学(理论化学)、化学物理学];
学科分类号
070304 ; 081704 ;
摘要
The chiral diamino-bis(bithiophene) ligands were firstly employed in the irridium(I)-catalyzed asymmetric transfer hydrogenation of aromatic ketones. The new catalyst systems, generated in situ from chiral diamino-bis(bithiophene) ligands and IrCl(CO)(PPh3)(2) in (PrOH)-Pr-i, gave the corresponding optically active secondary alcohols with high yield and fair to good enantioselectivities (up to 90% ee). The chiral Ir(I)/diamino-bis(bithiophene) complexes were also synthesized and characterized. The XPS spectra showed that the potentially multidentate ligands coordinated to the It atom through the nitrogen atoms, while the thiophene pendants did not participate in coordination to the It atom. (C) 2009 Elsevier B.V. All rights reserved.
引用
收藏
页码:149 / 153
页数:5
相关论文
共 38 条
[1]   Novel chiral diamino-oligothiophenes as valuable ligands in Pd-catalyzed allylic alkylations. On the "primary" role of "secondary" interactions in asymmetric catalysis [J].
Albano, VG ;
Bandini, M ;
Melucci, M ;
Monari, M ;
Piccinelli, F ;
Tommasi, S ;
Umani-Ronchi, A .
ADVANCED SYNTHESIS & CATALYSIS, 2005, 347 (11-13) :1507-1512
[2]   Thiophenes in organotransition metal chemistry: Patterns of reactivity [J].
Angelici, RJ .
ORGANOMETALLICS, 2001, 20 (07) :1259-1275
[3]   New chiral diamino-bis(tert-thiophene): an effective ligand for Pd- and Zn-catalyzed asymmetric transformations [J].
Bandini, Marco ;
Melucci, Manuela ;
Piccinelli, Fabio ;
Sinisi, Riccardo ;
Tommasi, Simona ;
Umani-Ronchi, Achille .
CHEMICAL COMMUNICATIONS, 2007, (43) :4519-4521
[4]   New recoverable poly(ethylene glycol)-supported C1-diamino-oligothiophene ligands for palladium-promoted asymmetric allylic alkylation (AAA) reactions [J].
Bandini, Marco ;
Benaglia, Maurizio ;
Quinto, Tommaso ;
Tommasi, Simona ;
Umani-Ronchi, Achille .
ADVANCED SYNTHESIS & CATALYSIS, 2006, 348 (12-13) :1521-1527
[5]   Homogeneous catalysis with transition metal complexes containing sulfur ligands [J].
Bayón, JC ;
Claver, C ;
Masdeu-Bultó, AM .
COORDINATION CHEMISTRY REVIEWS, 1999, 193-5 :73-145
[6]  
Beller M., 1998, TRANSITION METALS OR
[7]   Catalytic asymmetric synthesis of secondary alcohols using chiral cis-1-amino-2-hydroxy-1,2,3,4-tetrahydronaphthalene as chiral ligand [J].
Bellucci, CM ;
Bergamini, A ;
Cozzi, PG ;
Papa, A ;
Tagliavini, E ;
UmaniRonchi, A .
TETRAHEDRON-ASYMMETRY, 1997, 8 (06) :895-902
[8]   2,5-dimethyl-3,4-bis[(2R,5R)-2,5-dimethylphospholano]thiophene:: First member of the hetero-DuPHOS family [J].
Benincori, T ;
Pilati, T ;
Rizzo, S ;
Sannicolò, F ;
Burk, MJ ;
de Ferra, L ;
Ullucci, E ;
Piccolo, O .
JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (14) :5436-5441
[9]   A new modular class of easily accessible, inexpensive, and efficient chiral diphosphine ligands for homogeneous stereoselective catalysis [J].
Benincori, T ;
Gladiali, S ;
Rizzo, S ;
Sannicolò, F .
JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (17) :5940-5942
[10]   Cationic planar chiral palladium PS complexes as highly efficient catalysts in the enantioselective ring opening of oxa- and azabicyclic alkenes [J].
Cabrera, S ;
Arrayás, RG ;
Carretero, JC .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (30) :3944-3947