Rapid access to enantiopure bupropion and its major metabolite by stereospecific nucleophilic substitution on an α-ketotriflate

被引:85
作者
Fang, QK [1 ]
Han, ZX [1 ]
Grover, P [1 ]
Kessler, D [1 ]
Senanayake, CH [1 ]
Wald, SA [1 ]
机构
[1] Sepracor Inc, Chem Proc Res & Dev, Marlborough, MA 01752 USA
关键词
D O I
10.1016/S0957-4166(00)00349-9
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
A stereospecific method for the synthesis of enantiopure alpha -aminoketone from its corresponding alpha -hydroxy-ketone via the triflate intermediate is discussed. This strategy provides a rapid and efficient route for the preparation of either enantiomer of bupropion and its biologically active hydroxylated metabolite, (C) 2000 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:3659 / 3663
页数:5
相关论文
共 21 条
[1]   Synthesis of optically active α-hydroxy carbonyl compounds by the catalytic, enantioselective oxidation of silyl enol ethers and ketene acetals with (salen)manganese(III) complexes [J].
Adam, W ;
Fell, RT ;
Stegmann, VR ;
Saha-Möller, CR .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (04) :708-714
[2]   Synthesis, stereochemistry and anti-tetrabenazine activity of bicyclo analogues of 2-phenylmorpholines [J].
Boswell, GE ;
Musso, DL ;
Davis, AO ;
Kelley, JL ;
Soroko, FE ;
Cooper, BR .
JOURNAL OF HETEROCYCLIC CHEMISTRY, 1997, 34 (06) :1813-1820
[3]   A PSEUDOMONAS SP ALCOHOL-DEHYDROGENASE WITH BROAD SUBSTRATE-SPECIFICITY AND UNUSUAL STEREOSPECIFICITY FOR ORGANIC-SYNTHESIS [J].
BRADSHAW, CW ;
FU, H ;
SHEN, GJ ;
WONG, CH .
JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (05) :1526-1532
[4]  
Coppola G.M., 1997, ALPHA HYDROXY ACIDS
[6]   CHEMISTRY OF OXAZIRIDINES .14. ASYMMETRIC OXIDATION OF KETONE ENOLATES USING ENANTIOMERICALLY PURE (CAMPHORYLSULFONYL)OXAZIRIDINE [J].
DAVIS, FA ;
SHEPPARD, AC ;
CHEN, BC ;
HAQUE, MS .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (18) :6679-6690
[7]   ASYMMETRIC HYDROXYLATION OF ENOLATES WITH N-SULFONYLOXAZIRIDINES [J].
DAVIS, FA ;
CHEN, BC .
CHEMICAL REVIEWS, 1992, 92 (05) :919-934
[8]   ENZYMES IN ORGANIC-SYNTHESIS - LIPASE-CATALYZED RESOLUTION OF SECONDARY ALPHA-KETOALCOHOLS [J].
DUH, TH ;
WANG, YF ;
WU, MJ .
TETRAHEDRON-ASYMMETRY, 1993, 4 (08) :1793-1794
[9]  
EFFENBERGER F, 1986, LIEBIGS ANN CHEM, P334
[10]   Nucleophilic substitution on alpha-mesyloxy-O-alkyloximes .1. Enantiospecific synthesis of 2-(imidazol-1-yl)-1,3-diphenylpropan-1-one O-alkyloximes [J].
Giordani, A ;
Carera, A ;
Pinciroli, V ;
Cozzi, P .
TETRAHEDRON-ASYMMETRY, 1997, 8 (02) :253-263