Asymmetric catalysis.: Part 153:: Metal-catalysed enantioselective α-ketol rearrangement

被引：56
作者：
Brunner, H
Kagan, HB
Kreutzer, G
机构：
[1] Univ Regensburg, Inst Anorgan Chem, D-93040 Regensburg, Germany
[2] Univ Paris 11, Inst Chim Mol & Mat Orsay, F-91405 Orsay, France
来源：
TETRAHEDRON-ASYMMETRY | 2003年 / 14卷 / 15期
关键词：
D O I：
10.1016/S0957-4166(03)00433-6
中图分类号：
O61 [无机化学];
学科分类号：
070301 ; 081704 ;
摘要：
Promoted by catalytic amounts of Ni complexes tertiary alpha-hydroxyketones 1a, 3a-5a undergo rearrangement, forming chiral isomers 1b, 3b-5b. The best enantioselection was obtained with the model system 1-benzoylcyclopentanol 4a/2-hydroxy-2-phenylcyclohexanone 4b. In a ligand screening 2-[4-(S)-tert-butyloxazolin-2-yl]pyridine gave the highest enantiomeric excess of 46% (S)-4b. The analogous isomerisation reactions of alpha-hydroxyimines 6a, 7a forming chiral alpha-aminoketones 6b, 7b were established. (C) 2003 Elsevier Ltd. All rights reserved.
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页码：2177 / 2187
页数：11
相关论文
共 32 条
  • [21] KLOSE R, 2002, S KEMATIN
  • [22] KREUTZER G, 2003, THESIS U REGENSBURG
  • [23] COPPER(II) COMPLEXES WITH OPTICALLY-ACTIVE DIAMINES .1. SYNTHESIS AND PROPERTIES OF COPPER(II) COMPLEXES WITH N-BENZYL AND N-METHYL DERIVATIVES OF 1,2-DIAMINOPROPANE
    KURGANOV, AA
    DAVANKOV, VA
    ZHUCHKOVA, LY
    PONOMARYOVA, TM
    [J]. INORGANICA CHIMICA ACTA-ARTICLES, 1980, 39 (02): : 237 - 241
  • [24] MENHART V, 1992, Patent No. 277268
  • [25] MENZER M, 1985, Patent No. 217511
  • [26] HIGHLY ENANTIOSELECTIVE HYDROSILYLATION OF KETONES WITH CHIRAL AND C2-SYMMETRICAL BIS(OXAZOLINYL)PYRIDINE-RHODIUM CATALYSTS
    NISHIYAMA, H
    KONDO, M
    NAKAMURA, T
    ITOH, K
    [J]. ORGANOMETALLICS, 1991, 10 (02) : 500 - 508
  • [27] CHIRALITY RECOGNITION OF 1,1'-BI-2-NAPHTHOL WITH OPTICALLY-ACTIVE BIS(OXAZOLINYL)PYRIDINES
    NISHIYAMA, H
    TAJIMA, T
    TAKAYAMA, M
    ITOH, K
    [J]. TETRAHEDRON-ASYMMETRY, 1993, 4 (07) : 1461 - 1464
  • [28] Preiss D, 1995, Patent, Patent No. [DE4409671, 4409671]
  • [29] RUSSO T, 2001, Patent No. 0198265
  • [30] Steiner K., 1997, PCT Int. Appl. WO, Patent No. [9743244, 9743244 Al]
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