Organocatalytic asymmetric domino reactions:: A cascade consisting of a Michael addition and an aldehyde α-alkylation

被引:194
作者
Enders, Dieter [1 ]
Wang, Chuan [1 ]
Bats, Jan W. [2 ]
机构
[1] Rhein Westfal TH Aachen, Inst Organ Chem, D-52074 Aachen, Germany
[2] Goethe Univ Frankfurt, Inst Organ Chem & Chem Biol, D-60439 Frankfurt, Germany
关键词
alkylation; amino acids; domino reactions; organocatalysis; quaternary stereocenters;
D O I
10.1002/anie.200802532
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
(Chemical Equation Presented) A direct approach to cyclic γ-nitroaldehydes with an all-carbon-substituted quaternary stereocenter is provided by a novel organocatalytic diastereo- and enantioselective cascade consisting of a Michael addition and an aldehyde α-alkylation (see scheme). The corresponding γ-amino acids are available in two steps. © 2008 Wiley-VCH Verlag GmbH & Co. KGaA.
引用
收藏
页码:7539 / 7542
页数:4
相关论文
共 114 条
  • [1] Organocatalytic asymmetric conjugate additions
    Almasi, Diana
    Alonso, Diego A.
    Najera, Carmen
    [J]. TETRAHEDRON-ASYMMETRY, 2007, 18 (03) : 299 - 365
  • [2] [Anonymous], 2008, ANGEW CHEM, DOI DOI 10.1002/ANGE.200704684
  • [3] [Anonymous], 2004, ANGEW CHEM, V116, P1292
  • [4] Pregabalin pharmacology and its relevance to clinical practice
    Ben-Menachem, E
    [J]. EPILEPSIA, 2004, 45 : 13 - 18
  • [5] BERKESSEL A, 2004, ASYMMETRIC ORGANOCTA
  • [6] BERKESSEL A, 2004, ACC CHEM RES, V37
  • [7] Catalytic direct asymmetric Michael reactions: Taming naked aldehyde donors
    Betancort, JM
    Barbas, CF
    [J]. ORGANIC LETTERS, 2001, 3 (23) : 3737 - 3740
  • [8] Bryans JS, 1999, MED RES REV, V19, P149, DOI 10.1002/(SICI)1098-1128(199903)19:2<149::AID-MED3>3.0.CO
  • [9] 2-B
  • [10] Cabrera S., 2008, ANGEW CHEM, V120, P127