Highly Enantioselective Asymmetric Isomerization of Primary Allylic Alcohols with an Iridium-N,P Complex

被引：53
作者：
Li, Jia-Qi [1 ]
Peters, Byron [1 ]
Andersson, Pher G. [1 ,2 ]
机构：
[1] Uppsala Univ, Dept Biochem & Organ Chem, S-75123 Uppsala, Sweden
[2] Univ KwaZulu Natal, Sch Chem, Durban, South Africa
来源：
CHEMISTRY-A EUROPEAN JOURNAL | 2011年 / 17卷 / 40期
基金：
瑞典研究理事会;
关键词：
aldehydes; allylic alcohols; asymmetric catalysis; iridium; isomerization; N; P ligands; CATALYZED ISOMERIZATION; HYDROGENATION; LIGANDS; OLEFINS;
D O I：
10.1002/chem.201101524
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
Access to chiral aldehydes: The asymmetric isomerization of primary allylic alcohols was studied with a bicyclic phosphine-oxazoline iridium catalyst. This method displays a broad substrate scope and leads to the desired chiral aldehydes with excellent enantioselectivities (see scheme; R 1, R 2=Ar or alkyl). Copyright © 2011 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
引用
收藏
页码：11143 / 11145
页数：3
相关论文
共 26 条
  • [1] AKUTAGAWA S, 1999, COMPREHENSIVE ASYMME, V2, pCH23
  • [2] Akutagawa S., 2000, CATALYTIC ASYMMETRIC, P145
  • [3] Ruthenium-catalyzed isomerizations of allylic and propargylic alcohols in aqueous and organic media: Applications in synthesis
    Cadierno, Victorio
    Crochet, Pascale
    Gimeno, Jose
    [J]. SYNLETT, 2008, (08) : 1105 - 1124
  • [4] Development of new thiazole-based iridium catalysts and their applications in the asymmetric hydrogenation of trisubstituted olefins
    Cheruku, Pradeep
    Paptchikhine, Alexander
    Ali, Muhammad
    Neudorfl, Jorg-M.
    Andersson, Pher G.
    [J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2008, 6 (02) : 366 - 373
  • [5] Iridium catalysts for the asymmetric hydrogenation of olefins with nontraditional functional substituents
    Church, Tamara L.
    Andersson, Pher G.
    [J]. COORDINATION CHEMISTRY REVIEWS, 2008, 252 (5-7) : 513 - 531
  • [6] Iridium-catalyzed asymmetric hydrogenation of fluorinated olefins using N,P-ligands: A struggle with hydrogenolysis and selectivity
    Engman, Mattias
    Diesen, Jarle S.
    Paptchikhine, Alexander
    Andersson, Pher G.
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (15) : 4536 - +
  • [7] Fu GC, 2005, MODERN RHODIUM-CATALYZED ORGANIC REACTIONS, P79, DOI 10.1002/3527604693.ch4
  • [8] Ir-catalysed asymmetric hydrogenation:: Ligands, substrates and mechanism
    Kallström, K
    Munslow, I
    Andersson, PG
    [J]. CHEMISTRY-A EUROPEAN JOURNAL, 2006, 12 (12) : 3194 - 3200
  • [9] Rationally designed ligands for asymmetric iridium-catalyzed hydrogenation of olefins
    Källström, K
    Hedberg, C
    Brandt, P
    Bayer, A
    Andersson, PG
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (44) : 14308 - 14309
  • [10] Bicyclic phosphine-thiazole ligands for the asymmetric hydrogenation of olefins
    Li, Jia-Qi
    Paptchikhine, Alexander
    Govender, Thavendran
    Andersson, Pher G.
    [J]. TETRAHEDRON-ASYMMETRY, 2010, 21 (11-12) : 1328 - 1333
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