An efficient method to convert lactams and amides into 2,2-dialkylated amines

被引:39
作者
Agosti, Alessandro [1 ]
Britto, Sebastian [1 ]
Renaud, Philippe [1 ]
机构
[1] Univ Bern, Dept Chem & Biochem, CH-3012 Bern, Switzerland
关键词
D O I
10.1021/ol800145h
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A practical method for the synthesis of gern-2,2-disubstituted tertiary amines from the corresponding lactams (or amides) is reported. It is based on the reaction of thioiminium ions, easily prepared from lactams and amides with organometallic reagents such allylmagnesium, benzyl magnesium, and primary alkylcerium reagents.
引用
收藏
页码:1417 / 1420
页数:4
相关论文
共 20 条
  • [1] Enantioselective synthesis of piperidine, indolizidine, and quinolizidine alkaloids from a phenylglycinol-derived δ-lactam
    Amat, M
    Llor, N
    Hidalgo, J
    Escolano, C
    Bosch, J
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (05) : 1919 - 1928
  • [2] Armstrong S.K., 1998, J. Chem. Soc., V1, P371
  • [3] Recent approaches to the construction of 1-azaspiro[4.5]decanes and related 1-azaspirocycles
    Dake, G
    [J]. TETRAHEDRON, 2006, 62 (15) : 3467 - 3492
  • [4] Synthesis of oxygen- and nitrogen-containing heterocycles by ring-closing metathesis
    Deiters, A
    Martin, SF
    [J]. CHEMICAL REVIEWS, 2004, 104 (05) : 2199 - 2238
  • [5] Denton SM, 1999, SYNLETT, P55
  • [6] The reaction of organic halides with piperidine III Cyclohexyl bromide and the butyl bromides
    Drake, WV
    McElvain, SM
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1933, 55 : 1155 - 1158
  • [7] Ruthenium-catalyzed ionic hydrogenation of aziridinium cations
    Guan, HR
    Saddoughi, SA
    Shaw, AP
    Norton, JR
    [J]. ORGANOMETALLICS, 2005, 24 (26) : 6358 - 6364
  • [8] SYNTHESIS AND ABSOLUTE-CONFIGURATION OF THE ARISTOTELIA ALKALOID PEDUNCULARINE
    KLAVER, WJ
    HIEMSTRA, H
    SPECKAMP, WN
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (07) : 2588 - 2595
  • [9] KNABE J, 1963, ARCHIV PHARM BERICHT, V296, P820
  • [10] LATTES A, 1967, TETRAHEDRON LETT, P5165