Diastereo-and enantioselective synthesis of cis-2-hydroxycyclohexanamine and corresponding ethers by asymmetric reductive amination

被引:23
作者
Lauktien, G [1 ]
Volk, FJ [1 ]
Frahm, AW [1 ]
机构
[1] INST PHARMAZEUT,LEHRSTUHL PHARMAZEUT CHEM,D-79104 FREIBURG,GERMANY
关键词
D O I
10.1016/S0957-4166(97)00456-4
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
A series of homochiral cis-2-alkoxy- and 2-aryloxycyclohexanamines 5b-5e has been synthesised by means of asymmetric reductive amination of the corresponding racemic 2-oxygenated cyclohexanones 2 with ee-values ranging from 95 to >99%. The respective 2-hydroxy and 2-cyclohexyl derivatives 5g-5h have been prepared from the 2-phenoxycyclohexanamine 4e. Relative and absolute stereochemistry has been elucidated. (C) 1997 Elsevier Science Ltd.
引用
收藏
页码:3457 / 3466
页数:10
相关论文
共 28 条
[1]   Some reactions of Delta(2)-Cyclohexenone, including the synthesis of bicyclo(2,2,2)-octaniedione-2,6 [J].
Bartlett, PD ;
Woods, GF .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1940, 62 :2933-2938
[2]  
BERGMANN M, 1926, LIEBIGS ANN CHEM, V48, P448
[3]  
BRADLEY J, 1966, PHYSIOL, V183, P658
[4]  
BRINGMANN G, 1989, SYNTHESIS-STUTTGART, P608
[5]   ALPHA-METHOXY-ALPHA-TRIFLUOROMETHYLPHENYLACETIC ACID, A VERSATILE REAGENT FOR DETERMINATION OF ENANTIOMERIC COMPOSITION OF ALCOHOLS AND AMINES [J].
DALE, JA ;
DULL, DL ;
MOSHER, HS .
JOURNAL OF ORGANIC CHEMISTRY, 1969, 34 (09) :2543-&
[6]   STRUCTURE AND POSITION OF DIMER EQUILIBRIUM OF ALPHA ALKOXYCYCLOHEXANONES [J].
DURBECK, HW ;
FRISCHKO.CG ;
HILPERT, K .
TETRAHEDRON, 1971, 27 (13) :2927-&
[7]   ASYMMETRIC REDUCTIVE AMINATION OF CYCLOALKANONES, .3. INFLUENCE OF CATALYST AND REDUCING AGENT ON THE DIASTEREOSELECTIVITY AND ENANTIOSELECTIVITY [J].
KNUPP, G ;
FRAHM, AW .
ARCHIV DER PHARMAZIE, 1985, 318 (03) :250-257
[8]   ASYMMETRIC REDUCTIVE AMINATION OF CYCLOALKANONES .2. SYNTHESIS AND ABSOLUTE-CONFIGURATION OF 2-SUBSTITUTED CYCLOHEXANAMINES [J].
KNUPP, G ;
FRAHM, AW .
CHEMISCHE BERICHTE-RECUEIL, 1984, 117 (06) :2076-2098
[9]  
KNUPP G, 1982, THESIS BONN
[10]  
KOSOLAPOFF GM, 1964, CA 1770G, V61