Kinetic resolution of racemic secondary alcohols catalyzed by chiral diaminodiphosphine-Ir(I) complexes

被引:52
作者
Li, Yan-Yun [1 ]
Zhang, Xue-Qin
Dong, Zhen-Rong
Shen, Wei-Yi
Chen, Gui
Gao, Jing-Xing
机构
[1] Xiamen Univ, State Key Lab Phys Chem Solid Surfaces, Coll Chem & Chem Engn, Xiamen 361005, Fujian, Peoples R China
[2] Xiamen Univ, Dept Chem, Coll Chem & Chem Engn, Xiamen 361005, Fujian, Peoples R China
关键词
D O I
10.1021/ol062244f
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Chiral diaminodiphosphine-Ir(I) complexes were found to efficiently catalyze enantioselective oxidation of racemic secondary alcohols in acetone. In the presence of base, oxidative kinetic resolution of the alcohols proceeded smoothly with excellent enantioselectivity (up to 98% ee) under mild conditions.
引用
收藏
页码:5565 / 5567
页数:3
相关论文
共 33 条
[1]   Transition metal hydrides as active intermediates in hydrogen transfer reactions [J].
Bäckvall, JE .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2002, 652 (1-2) :105-111
[2]   Selective hydrogenation for fine chemicals: Recent trends and new developments [J].
Blaser, HU ;
Malan, C ;
Pugin, B ;
Spindler, F ;
Steiner, H ;
Studer, M .
ADVANCED SYNTHESIS & CATALYSIS, 2003, 345 (1-2) :103-151
[3]   Optimization or breakthrough?: The first highly cis- and enantioselective asymmetric cyclopropanation of 1-octene by "electronic and counterion" tuning of [RuCl(PNNP)]+ catalysts [J].
Bonaccorsi, C ;
Mezzetti, A .
ORGANOMETALLICS, 2005, 24 (21) :4953-4960
[4]   Asymmetric transfer hydrogenation of aromatic ketones catalyzed by the iridium hydride complex under ambient conditions [J].
Chen, JS ;
Li, YY ;
Dong, ZR ;
Li, BZ ;
Gao, JX .
TETRAHEDRON LETTERS, 2004, 45 (45) :8415-8418
[5]   Mechanisms of the H2-hydrogenation and transfer hydrogenation of polar bonds catalyzed by ruthenium hydride complexes [J].
Clapham, SE ;
Hadzovic, A ;
Morris, RH .
COORDINATION CHEMISTRY REVIEWS, 2004, 248 (21-24) :2201-2237
[6]   Highly efficient iridium catalyst for asymmetric transfer hydrogenation of aromatic ketones under base-free conditions [J].
Dong, ZR ;
Li, YY ;
Chen, JS ;
Li, BZ ;
Xing, Y ;
Gao, JX .
ORGANIC LETTERS, 2005, 7 (06) :1043-1045
[7]   Enantioselective routes to both enantiomers of aryl alcohols with a single catalyst antipode: Ru and Os transfer hydrogenation catalysts [J].
Faller, JW ;
Lavoie, AR .
ORGANIC LETTERS, 2001, 3 (23) :3703-3706
[8]   Recoverable catalysts for asymmetric organic synthesis [J].
Fan, QH ;
Li, YM ;
Chan, ASC .
CHEMICAL REVIEWS, 2002, 102 (10) :3385-3465
[9]   Cationic rhodium complexes with chiral tetradentate ligands as catalysts for enantioselective reduction of simple ketones [J].
Gao, JX ;
Yi, XD ;
Xu, PP ;
Tang, CL ;
Zhang, H ;
Wan, HL ;
Ikariya, T .
JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 2000, 159 (01) :3-9
[10]   A ruthenium(II) complex with a C-2-symmetric diphosphine/diamine tetradentate ligand for asymmetric transfer hydrogenation of aromatic ketones [J].
Gao, JX ;
Ikariya, T ;
Noyori, R .
ORGANOMETALLICS, 1996, 15 (04) :1087-1089