A new practical asymmetric synthesis of C-2-symmetrical 1,1'-ferrocenyl diols via CBS-reduction

被引:64
作者
Schwink, L [1 ]
Knochel, P [1 ]
机构
[1] UNIV MARBURG,FACHBEREICH CHEM,D-35032 MARBURG,GERMANY
关键词
D O I
10.1016/0040-4039(95)02098-5
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
CBS-reduction of ferrocenyl diketones 3 provides C-2-symmetrical ferrocenyl diols (R,R)-1 in > 98% ee accompanied by small amounts of the meso-diols (R,S)-1. The utility of 1 for the preparation of various potential ligands for asymmetric catalysis such as 9, 12, 13 and 14 is demonstrated.
引用
收藏
页码:25 / 28
页数:4
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共 26 条
  • [11] ASYMMETRIC-SYNTHESIS CATALYZED BY CHIRAL FERROCENYLPHOSPHINE-TRANSITION METAL-COMPLEXES .1. PREPARATION OF CHIRAL FERROCENYLPHOSPHINES
    HAYASHI, T
    MISE, T
    FUKUSHIMA, M
    KAGOTANI, M
    NAGASHIMA, N
    HAMADA, Y
    MATSUMOTO, A
    KAWAKAMI, S
    KONISHI, M
    YAMAMOTO, K
    KUMADA, M
    [J]. BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1980, 53 (04) : 1138 - 1151
  • [12] AN ASYMMETRIC-SYNTHESIS OF MK-0417 - OBSERVATIONS ON OXAZABOROLIDINE-CATALYZED REDUCTIONS
    JONES, TK
    MOHAN, JJ
    XAVIER, LC
    BLACKLOCK, TJ
    MATHRE, DJ
    SOHAR, P
    JONES, ETT
    REAMER, RA
    ROBERTS, FE
    GRABOWSKI, EJJ
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (02) : 763 - 769
  • [13] Noyori R., 1994, ASYMMETRIC CATALYSIS
  • [14] Ojima I., 2010, CATALYTIC ASYMMETRIC
  • [15] SYNTHESIS OF 4(S)-(3,4-DICHLOROPHENYL)-3,4-DIHYDRO-1(2H)-NAPHTHALENONE BY SN2 CUPRATE DISPLACEMENT OF AN ACTIVATED CHIRAL BENZYLIC ALCOHOL
    QUALLICH, GJ
    WOODALL, TM
    [J]. TETRAHEDRON, 1992, 48 (47) : 10239 - 10248
  • [16] A COMBINED SYNTHETIC AND AB-INITIO STUDY OF CHIRAL OXAZABOROLIDINES STRUCTURE AND ENANTIOSELECTIVITY RELATIONSHIPS
    QUALLICH, GJ
    BLAKE, JF
    WOODALL, TM
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (19) : 8516 - 8525
  • [17] STRONG ELECTRONIC EFFECTS ON ENANTIOSELECTIVITY IN RHODIUM-CATALYZED HYDROBORATIONS WITH NOVEL PYRAZOLE-CONTAINING FERROCENYL LIGANDS
    SCHNYDER, A
    HINTERMANN, L
    TOGNI, A
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1995, 34 (08): : 931 - 933
  • [18] SCHWINK L, 1995, IN PRESS ORGANOMETAL, V14
  • [19] SINGH VK, 1992, SYNTHESIS-STUTTGART, P605
  • [20] ASYMMETRIC-SYNTHESIS OF CHIRAL SECONDARY ALCOHOLS WITH ISOPROPYL SUBSTITUENTS BY THE CATALYTIC ENANTIOSELECTIVE ADDITION OF DIISOPROPYLZINC TO ALDEHYDES USING N,N-DIALKYLNOREPHEDRINES AS CHIRAL CATALYSTS
    SOAI, KS
    HAYASE, T
    TAKAI, K
    SUGIYAMA, T
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (25) : 7908 - 7909