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
  • [1] Asymmetric synthesis of vicinal amino alcohols: xestoaminol C, sphinganine and sphingosine
    Abraham, Elin
    Davies, Stephen G.
    Millican, Nicholas L.
    Nicholson, Rebecca L.
    Roberts, Paul M.
    Smith, Andrew D.
    [J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2008, 6 (09) : 1655 - 1664
  • [2] 1,2-amino alcohols and their heterocyclic derivatives as chiral auxiliaries in asymmetric synthesis
    Ager, DJ
    Prakash, I
    Schaad, DR
    [J]. CHEMICAL REVIEWS, 1996, 96 (02) : 835 - 875
  • [3] Ager DJ, 1997, ALDRICHIM ACTA, V30, P3
  • [4] Palladium-catalyzed ring-forming aminoacetoxylation of alkenes
    Alexanian, EJ
    Lee, C
    Sorensen, EJ
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (21) : 7690 - 7691
  • [5] Synthesis of D/L-erythro-Sphingosine Using a Tethered Aminohydroxylation Reaction as the Key Step
    Antonio Morales-Sema, Jose
    Diaz, Yolanda
    Isabel Matheu, M.
    Castillon, Sergio
    [J]. SYNTHESIS-STUTTGART, 2009, (05): : 710 - 712
  • [6] BACKVALL JE, 1980, J ORG CHEM, V45, P2893
  • [7] BACKVALL JE, 1975, TETRAHEDRON LETT, P2225
  • [8] BACKVALL JE, 1982, J ORG CHEM, V47, P1126
  • [9] Bagii J.F., 1973, J. Org. Chem, V38, P1253
  • [10] Catalytic Oxyamidation of Indoles
    Beaumont, Stephane
    Pons, Valerie
    Retailleau, Pascal
    Dodd, Robert H.
    Dauban, Philippe
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2010, 49 (09) : 1634 - 1637