An Asymmetric Organocatalytic Quadruple Domino Reaction Employing a Vinylogous Friedel-Crafts/Michael/Michael/Aldol Condensation Sequence

被引：10
作者：
Philipps, Arne R. [1 ]
Fritze, Lars [1 ]
Erdmann, Nico [1 ]
Enders, Dieter [1 ]
机构：
[1] Rhein Westfal TH Aachen, Inst Organ Chem, D-52074 Aachen, Germany
来源：
SYNTHESIS-STUTTGART | 2015年 / 47卷 / 16期
基金：
欧洲研究理事会;
关键词：
organocatalysis; domino reaction; quadruple cascade; asymmetric catalysis; alkenylation; DIPHENYLPROLINOL SILYL ETHER; TRICYCLIC CARBON FRAMEWORKS; INFRARED ABSORBING DYES; CASCADE REACTIONS; MICHAEL-ALDOL; ENANTIOSELECTIVE SYNTHESIS; FUNCTIONALIZED CYCLOHEXANES; STEREOCENTERS; CONSTRUCTION; DERIVATIVES;
D O I：
10.1055/s-0034-1380197
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
An organocatalytic quadruple cascade initiated by a Friedel-Crafts-type reaction is described. The (S)-diphenylprolinol trimethylsilyl ether catalyzed reaction yields highly functionalized cyclohexenecarbaldehydes bearing a 1,1-bis[4-(dialkylamino)phenyl]ethene moiety and three contiguous stereogenic centers. The reaction tolerates various functional groups and all products are obtained with very good diastereoselectivity and with virtually complete enantiomeric excess.
引用
收藏
页码：2377 / 2384
页数：8
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    Wu, Li-Yuan
    Mazzanti, Andrea
    Giannichi, Berardino
    Pesciaioli, Fabio
    Song, Mao-Ping
    Bartoli, Giuseppe
    Melchiorre, Paolo
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (39) : 7200 - 7203
  • [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] Tandem and domino catalytic strategies for enantioselective synthesis
    Chapman, Christopher J.
    Frost, Christopher G.
    [J]. SYNTHESIS-STUTTGART, 2007, (01): : 1 - 21
  • [5] Vinylogous Organocatalytic Triple Cascade Reaction: Forging Six Stereocenters in Complex Spiro-Oxindolic Cyclohexanes
    Chatterjee, Indranil
    Bastida, David
    Melchiorre, Paolo
    [J]. ADVANCED SYNTHESIS & CATALYSIS, 2013, 355 (16) : 3124 - 3130
  • [6] Enantioselective Organocatalytic Conjugate Addition of Alkenes to α,β-Enones
    Cui, Lingyun
    Zhang, Long
    Luo, Sanzhong
    Cheng, Jin-Pei
    [J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2014, 2014 (17) : 3540 - 3545
  • [7] Primary-Tertiary Diamine/BrOnsted Acid Catalyzed C-C Coupling between para-Vinylanilines and Aldehydes
    Cui, Lingyun
    Zhu, Yunbo
    Luo, Sanzhong
    Cheng, Jin-Pei
    [J]. CHEMISTRY-A EUROPEAN JOURNAL, 2013, 19 (29) : 9481 - 9484
  • [8] Organocatalytic synthesis of drugs and bioactive natural products
    de Figueiredo, Renata Marcia
    Christmann, Mathias
    [J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2007, 2007 (16) : 2575 - 2600
  • [9] One-Pot Formation of Chiral Polysubstituted 3,4-Dihydropyrans via a Novel Organocatalytic Domino Sequence Involving Alkynal Self-Condensation
    Dong, Li-Jin
    Fan, Tian-Tian
    Wang, Chao
    Sun, Jian
    [J]. ORGANIC LETTERS, 2013, 15 (01) : 204 - 207
  • [10] Asymmetric synthesis of polyfunctionalized mono-, bi-, and tricyclic carbon frameworks via organocatalytic domino reactions
    Enders, Dieter
    Huettl, Matthias R. M.
    Raabe, Gerhard
    Bats, Jan W.
    [J]. ADVANCED SYNTHESIS & CATALYSIS, 2008, 350 (02) : 267 - 279
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