Self-Relay Gold(I)-Catalyzed Pictet-Spengler/Cyclization Cascade Reaction for the Rapid Elaboration of Pentacyclic Indole Derivatives

被引：35

作者：

Gobe, Valerian ^{[1
]}

Retailleau, Pascal ^{[1
]}

Guinchard, Xavier ^{[1
]}

机构：

[1] Univ Paris Saclay, Univ Paris 11, Inst Chim Subst Nat, CNRS UPR 2301, F-91198 Gif Sur Yvette, France

来源：

CHEMISTRY-A EUROPEAN JOURNAL | 2015年 / 21卷 / 49期

关键词：

cascade reaction; gold catalysis; homogenous catalysis; indoles; nitrogen heterocycles; TETRAHYDRO-BETA-CARBOLINES; BRONSTED ACID CATALYSTS; SPENGLER REACTION; TANDEM CATALYSIS; GOLD CATALYSIS; ENANTIOSELECTIVE SYNTHESIS; PROPARGYLIC ESTERS; CYCLIZATION; REARRANGEMENT; ALDEHYDES;

D O I：

10.1002/chem.201503941

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Gold-catalyzed cascade reactions allow the rapid elaboration of pentacyclic indolo[2,3-a]quinolizidines from N-allyl tryptamines and ortho-alkynylarylaldehydes. The tandem process combines a gold-catalyzed Pictet-Spengler reaction and a cyclization occurring concomitantly with an allyl transfer from the nitrogen atom to the stilbene function. Various substituted allyls were successfully transferred, furnishing the products in yields typically ranging from 60-98% in high diastereoselectivity. Tryptamines bearing a butenol chain undergo an additional cyclization to chiral hemiaminals in high diastereoselectivities.

引用

页码：17587 / 17590

页数：4

共 75 条

[1] [3,3]-Sigmatropic Rearrangement Step in the Gold-Catalyzed Cyclization of Allyl-(ortho-alkinylphenyl)methyl Ethers [J].

Ackermann, Martin ;

Bucher, Janina ;

Rappold, Melissa ;

Graf, Katharina ;

Rominger, Frank ;

Hashmi, A. Stephen K. .

CHEMISTRY-AN ASIAN JOURNAL, 2013, 8 (08) :1786-1794

[2] Two birds with one metallic stone: Single-pot catalysis of fundamentally different transformations [J].

Ajamian, A ;

Gleason, JL .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (29) :3754-3760

[3]

Ajamian A., 2004, Angew. Chem, V116, P3842

[4]

[Anonymous], ANGEW CHEM, DOI DOI 10.1002/ANGE.200704729

[5] Alternative synthetic methods through new developments in catalysis by gold [J].

Arcadi, Antonio .

CHEMICAL REVIEWS, 2008, 108 (08) :3266-3325

[6] Biogenetically inspired enantioselective approach to indolo[2,3-a]- and benzo[a]quinolizidine alkaloids from a synthetic equivalent of secologanin [J].

Bassas, O ;

Llor, N ;

Santos, MMM ;

Griera, R ;

Molins, E ;

Amat, M ;

Bosch, J .

ORGANIC LETTERS, 2005, 7 (14) :2817-2820

[7] Golden opportunities in stereoselective catalysis [J].

Bongers, Nadine ;

Krause, Norbert .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (12) :2178-2181

[8] Enantioselective synthesis of hexahydrofuro[3,2-c] quinolines through a multicatalytic and multicomponent process. A new "aromatic sandwich" model for BINOL-phosphoric acid catalyzed reactions [J].

Calleja, Jonas ;

Gonzalez-Perez, Adan B. ;

de Lera, Angel R. ;

Alvarez, Rosana ;

Fananas, Francisco J. ;

Rodriguez, Felix .

CHEMICAL SCIENCE, 2014, 5 (03) :996-1007

[9]

Cariou K., 2007, ANGEW CHEM, V119, P1913

[10] From PtCl2- and acid-catalyzed to uncatalyzed cycloisomerization of 2-propargyl anilines:: Access to functionalized indoles [J].

Cariou, Kevin ;

Ronan, Baptiste ;

Mignani, Serge ;

Fensterbank, Louis ;

Malacria, Max .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (11) :1881-1884

← 1 2 3 4 5 6 7 8 →