Stereoselective reductive amination of chiral N,N-Dibenzylamino ketones

被引:9
作者
Reetz, MT
Schmitz, A
机构
[1] Max Planck Inst Kohlenforsch, D-45470 Mulheim, Germany
[2] Univ Marburg, Fachbereich Chem, D-35043 Marburg, Germany
关键词
amino acids; diamines; asymmetric induction; reduction;
D O I
10.1016/S0040-4039(99)00360-3
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
N,N-Dibenzylamino ketones of the type Bn2N(R)CHC(O)CH3, prepared in enantiomerically pure form from alpha-amino acids, undergo stereoselective reductive amination using PhCH2NH2/NaCNBH3 or NH4OAc/NaCNBH3 with formation of diastereo- and enantiomerically pure vicinal diamines Bn2N(R)CHCH(NHCH2Ph)CH3 or Bn2N(R)CHCH(NH2)CH3, respectively. (C) 1999 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:2741 / 2742
页数:2
相关论文
共 18 条
[1]   2-AMINO-4-THIAZOLYL ACETIC-ACID DERIVATIVES OF CEPHALOSPORINS - EFFECT OF PRESENCE AND CONFIGURATION OF AN OXYIMINO GROUP ON ANTIBACTERIAL ACTIVITY [J].
BUCOURT, R ;
HEYMES, R ;
LUTZ, A ;
PENASSE, L ;
PERRONNET, J .
TETRAHEDRON, 1978, 34 (14) :2233-2243
[2]   HIGHLY ENANTIOSELECTIVE AND DIASTEREOSELECTIVE IRELAND-CLAISEN REARRANGEMENT OF ACHIRAL ALLYLIC ESTERS [J].
COREY, EJ ;
LEE, DH .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (10) :4026-4028
[3]  
Lucet D, 1998, ANGEW CHEM INT EDIT, V37, P2581, DOI 10.1002/(SICI)1521-3773(19981016)37:19<2580::AID-ANIE2580>3.0.CO
[4]  
2-L
[5]  
Lucet D., 1998, ANGEW CHEM, V110, P2724
[6]   TETRAPONERINES, TOXIC ALKALOIDS IN THE VENOM OF THE NEO-GUINEAN PSEUDOMYRMECINE ANT TETRAPONERA SP [J].
MERLIN, P ;
BRAEKMAN, JC ;
DALOZE, D ;
PASTEELS, JM .
JOURNAL OF CHEMICAL ECOLOGY, 1988, 14 (02) :517-527
[7]   NEW CONFORMATIONALLY RESTRICTED TC-99M N2S2 COMPLEXES AS MYOCARDIAL PERFUSION IMAGING AGENTS [J].
OHMOMO, Y ;
FRANCESCONI, L ;
KUNG, MP ;
KUNG, HF .
JOURNAL OF MEDICINAL CHEMISTRY, 1992, 35 (01) :157-162
[8]  
Reetz M. T., 1991, ANGEW CHEM, V103, P76
[9]  
REETZ MT, 1994, SYNTHESIS-STUTTGART, P733
[10]   NONRACEMIZING SYNTHESIS AND STEREOSELECTIVE REDUCTION OF CHIRAL ALPHA-AMINO KETONES [J].
REETZ, MT ;
DREWES, MW ;
LENNICK, K ;
SCHMITZ, A ;
HOLDGRUN, X .
TETRAHEDRON-ASYMMETRY, 1990, 1 (06) :375-378