Dynamic kinetic resolution allows a highly enantioselective synthesis of cis-α-aminocycloalkanols by ruthenium-catalyzed asymmetric hydrogenation

被引:58
作者
Liu, Sheng
Xie, Jian-Hua
Wang, Li-Xin
Zhou, Qi-Lin [1 ]
机构
[1] Nankai Univ, State Key Lab, Tianjin 300071, Peoples R China
[2] Nankai Univ, Inst Elementoorgan Chem, Tianjin 300071, Peoples R China
关键词
amino alcohols; asymmetric catalysis; diamines; hydrogenation; ruthenium; EFFICIENT SYNTHESIS; ORGANIC-SYNTHESIS; METAL-COMPLEXES; DERIVATIVES; KETONES; ALCOHOLS; LIGANDS;
D O I
10.1002/anie.200702491
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
(Chemical Equation Presented) Resolutely dynamic hydrogenation: A highly efficient asymmetric hydrogenation of racemic N,N-disubstituted α-aminocycloalkanones involving dynamic kinetic resolution in the presence of a ruthenium catalyst gives chiral α-aminocycloalkanols with excellent enantioselectivities and cis diastereoselectivities (see scheme). A synthesis of optically pure U-(-)-50488 based on this reaction is reported. © 2007 Wiley-VCH Verlag GmbH & Co. KGaA.
引用
收藏
页码:7506 / 7508
页数:3
相关论文
共 39 条
[1]   1,2-amino alcohols and their heterocyclic derivatives as chiral auxiliaries in asymmetric synthesis [J].
Ager, DJ ;
Prakash, I ;
Schaad, DR .
CHEMICAL REVIEWS, 1996, 96 (02) :835-875
[2]   General asymmetric hydrogenation of α-branched aromatic ketones catalyzed by TolBINAP/DMAPEN-ruthenium(II) complex [J].
Arai, Noriyoshi ;
Ooka, Hirohito ;
Azuma, Keita ;
Yabuuchi, Toshio ;
Kurono, Nobuhito ;
Inoue, Tsutomu ;
Ohkuma, Takeshi .
ORGANIC LETTERS, 2007, 9 (05) :939-941
[3]   The synthesis of vicinal amino alcohols [J].
Bergmeier, SC .
TETRAHEDRON, 2000, 56 (17) :2561-2576
[4]  
Ghosh AK, 1998, SYNTHESIS-STUTTGART, P937, DOI 10.1055/s-1998-2092
[5]   Chemoenzymatic preparation of optically active trans-cyclohexane-1,2-diamine derivatives:: An efficient synthesis of the analgesic U-(-)-50,488 [J].
González-Sabín, J ;
Gotor, V ;
Rebolledo, F .
CHEMISTRY-A EUROPEAN JOURNAL, 2004, 10 (22) :5788-5794
[6]   A biocatalytic approach to synthesizing optically active orthogonally protected trans-cyclopentane-1,2-diamine derivatives [J].
Gonzalez-Sabin, Javier ;
Gotor, Vicente ;
Rebolledo, Francisca .
JOURNAL OF ORGANIC CHEMISTRY, 2007, 72 (04) :1309-1314
[7]  
HAYASHI T, 1979, TETRAHEDRON LETT, P425
[8]   ASYMMETRIC-SYNTHESIS CATALYZED BY TRANSITION-METAL COMPLEXES WITH FUNCTIONALIZED CHIRAL FERROCENYLPHOSPHINE LIGANDS [J].
HAYASHI, T ;
KUMADA, M .
ACCOUNTS OF CHEMICAL RESEARCH, 1982, 15 (12) :395-401
[9]  
JACOBSON EN, 1999, COMP ASYMMETRIC CATA
[10]   Facile monoprotection of trans-1,2-diaminocyclohexane [J].
Kaik, M ;
Gawronski, J .
TETRAHEDRON-ASYMMETRY, 2003, 14 (11) :1559-1563