Organocatalytic asymmetric 5-hydroxypyrrolidine synthesis:: a highly enantioselective route to 3-substituted proline derivatives

被引：50
作者：
Rios, Ramon [1 ]
Ibrahem, Ismail [1 ]
Vesely, Jan [1 ]
Sunden, Henrik [1 ]
Cordova, Armando [1 ]
机构：
[1] Stockholm Univ, Arrhenius Lab, Dept Organ Chem, SE-10691 Stockholm, Sweden
来源：
TETRAHEDRON LETTERS | 2007年 / 48卷 / 49期
关键词：
D O I：
10.1016/j.tetlet.2007.10.028
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The highly enantioselective organocatalytic tandem reaction between 2-acylaminomalonates and alpha,beta-unsaturated aldehydes is presented. The reaction is a direct entry to 5-hydroxypyrrolidines and 3-substituted proline derivatives, which are furnished in high yields and 90-99% ee. (c) 2007 Elsevier Ltd. All rights reserved.
引用
收藏
页码：8695 / 8699
页数：5
相关论文
共 49 条
  • [1] Organocatalytic conjugate addition of malonates to α,β-unsaturated aldehydes:: Asymmetric formal synthesis of (-)-paroxetine, chiral lactams, and lactones
    Brandau, Sven
    Landa, Aitor
    Franzen, Johan
    Marigo, Mauro
    Jorgensen, Karl Anker
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (26) : 4305 - 4309
  • [2] A new approach for an organocatalytic multicomponent domino asymmetric reaction
    Carlone, Armando
    Cabrera, Silvia
    Marigo, Mauro
    Jorgensen, Karl Anker
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (07) : 1101 - 1104
  • [3] A simple asymmetric organocatalytic approach to optically active cyclohexenones
    Carlone, Armando
    Marigo, Mauro
    North, Chris
    Landa, Aitor
    Jorgensen, Karl Anker
    [J]. CHEMICAL COMMUNICATIONS, 2006, (47) : 4928 - 4930
  • [4] CONFORMATIONALLY CONSTRAINED AMINO-ACIDS - SYNTHESIS AND OPTICAL RESOLUTION OF 3-SUBSTITUTED PROLINE DERIVATIVES
    CHUNG, JYL
    WASICAK, JT
    ARNOLD, WA
    MAY, CS
    NADZAN, AM
    HOLLADAY, MW
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (01) : 270 - 275
  • [5] MODIFIED PROLINE SYNTHESIS
    COX, DA
    MAUGER, AB
    JOHNSON, AW
    [J]. JOURNAL OF THE CHEMICAL SOCIETY, 1964, (DEC): : 5024 - &
  • [6] Regio- and stereoselective Heck arylations of N-carbomethoxy-L-3-dehydroproline methyl ester with arenediazonium salts.: Total synthesis of neuroexcitatory aryl kainoids
    da Silva, Kezia Peixoto
    Godoi, Marla Narciso
    Duarte Correia, Carlos Roque
    [J]. ORGANIC LETTERS, 2007, 9 (15) : 2815 - 2818
  • [7] Dalko PI, 2001, ANGEW CHEM INT EDIT, V40, P3726, DOI 10.1002/1521-3773(20011015)40:20<3726::AID-ANIE3726>3.0.CO
  • [8] 2-D
  • [9] In the golden age of organocatalysis
    Dalko, PI
    Moisan, L
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (39) : 5138 - 5175
  • [10] Enantioselective synthesis of antiinfluenza compound A-315675
    DeGoey, DA
    Chen, HJ
    Flosi, WJ
    Grampovnik, DJ
    Yeung, CM
    Klein, LL
    Kempf, DJ
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (16) : 5445 - 5453
12345