One-pot organocatalytic direct asymmetric synthesis of γ-amino alcohol derivatives

被引:91
作者
Córdova, A [1 ]
机构
[1] Scripps Res Inst, La Jolla, CA 92037 USA
关键词
asymmetric synthesis; asymmetric catalysis; Mannich reactions; aldehydes; imines;
D O I
10.1055/s-2003-41423
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
This report describes the unprecedented use of unmodified aldehydes as donors in catalytic three component one-Pot asymmetric Mannich reactions. The Mannich-type reactions were also readily performed for the first time with both in situ generated and preformed N-PMP protected aromatic aldimines. The prolinecatalyzed reactions provided an efficient and very mild entry to either enantiomer of gamma-amino alcohol derivatives in high yield and stereoselectivity.
引用
收藏
页码:1651 / 1654
页数:4
相关论文
共 52 条
  • [1] Arend M, 1998, ANGEW CHEM INT EDIT, V37, P1044, DOI 10.1002/(SICI)1521-3773(19980504)37:8<1044::AID-ANIE1044>3.0.CO
  • [2] 2-E
  • [3] Diastereospecific synthesis of enantiomerically pure polysubstituted azetidines from 1,3-amino alcohols with three chiral centers
    Barluenga, J
    FernandezMari, F
    Viado, AL
    Aguilar, E
    Olano, B
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (16) : 5659 - 5662
  • [4] Direct catalytic asymmetric aldol reactions of aldehydes
    Bogevig, A
    Kumaragurubaran, N
    Jorgensen, KA
    [J]. CHEMICAL COMMUNICATIONS, 2002, (06) : 620 - 621
  • [5] Bogevig A, 2002, ANGEW CHEM INT EDIT, V41, P1790, DOI 10.1002/1521-3773(20020517)41:10<1790::AID-ANIE1790>3.0.CO
  • [6] 2-Y
  • [7] Direct organocatalytic aldol reactions in buffered aqueous media
    Córdova, A
    Notz, W
    Barbas, CF
    [J]. CHEMICAL COMMUNICATIONS, 2002, (24) : 3024 - 3025
  • [8] Direct organocatalytic asymmetric Mannich-type reactions in aqueous media:: one-pot Mannich-allylation reactions
    Córdova, A
    Barbas, CF
    [J]. TETRAHEDRON LETTERS, 2003, 44 (09) : 1923 - 1926
  • [9] anti-selective SMP-catalyzed direct asymmetric Mannich-type reactions:: synthesis of functionalized amino acid derivatives
    Córdova, A
    Barbas, CF
    [J]. TETRAHEDRON LETTERS, 2002, 43 (43) : 7749 - 7752
  • [10] Proline-catalyzed one-step asymmetric synthesis of 5-hydroxy-(2E)-hexenal from acetaldehyde
    Córdova, A
    Notz, W
    Barbas, CF
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (01) : 301 - 303