Recent Developments in Methodology for the Direct Oxyamination of Olefins

被引:240
作者
Donohoe, Timothy J. [1 ]
Callens, Cedric K. A. [1 ]
Flores, Aida [1 ]
Lacy, Adam R. [1 ]
Rathi, Akshat H. [1 ]
机构
[1] Univ Oxford, Dept Chem, Chem Res Lab, Oxford OX1 3TA, England
关键词
1,2-aminodiol; amino alcohols; alkenes; catalysis; oxyamination; TETHERED AMINOHYDROXYLATION TA; VICINAL AMINO-ALCOHOLS; SHARPLESS ASYMMETRIC AMINOHYDROXYLATION; HYPERVALENT IODINE COMPOUNDS; ENANTIOSELECTIVE SYNTHESIS; CHIRAL AUXILIARIES; INTRAMOLECULAR AMINOOXYGENATION; CATALYZED AMINOHYDROXYLATION; STEREOSELECTIVE-SYNTHESIS; OXIDATIVE CYCLIZATION;
D O I
10.1002/chem.201002323
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
1,2-Amino alcohols are high-value, versatile functional groups that are found in scores of biologically active molecules and other interesting synthetic targets such as ligands and auxiliaries. Given their prominent position within organic compounds of import, it is no surprise to note that many routes have been developed to access this motif and there are many different starting points from which a synthetic chemist might embark on a synthesis. However, one particular approach stands out from the others, and this is the direct conversion of an alkene to a vicinal amino alcohol derivative (oxyamination). Research in this field has been particularly active in recent years and many interesting new methodologies have been reported. The purpose of this review is to give the reader a tour of the methods that have emerged in the last few years so one can appreciate the myriad of different metals and reagents that can accomplish the oxyamination of alkenes. There are still many challenges to be overcome and, herein, we also outline the areas that are ripe for further development and which bode well for the future.
引用
收藏
页码:58 / 76
页数:19
相关论文
共 123 条
  • [111] Synthesis of small tripeptide molecules through a catalysis sequence comprising metathesis and aminohydroxylation
    Streuff, Jan
    Nieger, Martin
    Muniz, Kilian
    [J]. CHEMISTRY-A EUROPEAN JOURNAL, 2006, 12 (16) : 4362 - 4371
  • [112] A highly stereocontrolled total synthesis of dysiherbaine
    Takahashi, Keisuke
    Matsumura, Takashi
    Ishihara, Jun
    Hatakeyama, Susumi
    [J]. CHEMICAL COMMUNICATIONS, 2007, (40) : 4158 - 4160
  • [113] TAN C, 1967, CANCER-AM CANCER SOC, V20, P333, DOI 10.1002/1097-0142(1967)20:3<333::AID-CNCR2820200302>3.0.CO
  • [114] 2-K
  • [115] Chemo-enzymatic synthesis of new ferrocenyl-oxazolidinones and their application as chiral auxiliaries
    Ueberbacher, Bernhard J.
    Griengl, Herfried
    Weber, Hansjoerg
    [J]. TETRAHEDRON-ASYMMETRY, 2008, 19 (07) : 838 - 846
  • [116] BESTATIN, AN INHIBITOR OF AMINOPEPTIDASE-B, PRODUCED BY ACTINOMYCETES
    UMEZAWA, H
    AOYAGI, T
    SUDA, H
    HAMADA, M
    TAKEUCHI, T
    [J]. JOURNAL OF ANTIBIOTICS, 1976, 29 (01) : 97 - 99
  • [117] Total synthesis and conformational studies of hapalosin, N-desmethylhapalosin and 8-deoxyhapalosin
    Wagner, B
    Gonzalez, GI
    Dau, METH
    Zhu, JP
    [J]. BIOORGANIC & MEDICINAL CHEMISTRY, 1999, 7 (05) : 737 - 747
  • [118] Intramolecular Oxamidation of Unsaturated O-Alkyl Hydroxamates: A Remarkably Versatile Entry to Hydroxy Lactams
    Wardrop, Duncan J.
    Bowen, Edward G.
    Forslund, Raymond E.
    Sussman, Adam D.
    Weerasekera, Samanthi L.
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (04) : 1188 - +
  • [119] Iron-Catalyzed Aminohydroxylation of Olefins
    Williamson, Kevin S.
    Yoon, Tehshik P.
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (13) : 4570 - +
  • [120] Wirth T, 1999, SYNTHESIS-STUTTGART, P1271