Understanding the Role of Spiroindolenines in Pictet-Spengler Reactions

被引：5

作者：

Unsworth, William P. ^{[1
]}

机构：

[1] Univ York, Dept Chem, York YO10 5DD, N Yorkshire, England

来源：

CHEM | 2018年 / 4卷 / 08期

基金：

英国工程与自然科学研究理事会;

关键词：

CYCLIZATION; TRYPTAMINES; DERIVATIVES;

D O I：

10.1016/j.chempr.2018.07.012

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Despite being discovered over a century ago, a unified mechanistic understanding of the Pictet-Spengler reaction continues to elude us. In this issue of Chem, Zheng et al. go a long way toward finally answering this long-standing and occasionally controversial mechanistic puzzle by combining density functional theory with molecular dynamics in an innovative analysis.

引用

页码：1767 / 1770

页数：4

共 10 条

[1] Reactions Involving Tryptamines and -Allenyl Aldehydes: Competition between Pictet-Spengler Reaction and Cyclization to 1-Aminotetralins [J].

Gobe, Valerian ;

Gandon, Vincent ;

Guinchard, Xavier .

ADVANCED SYNTHESIS & CATALYSIS, 2018, 360 (06) :1280-1288

[2] Gold and BINOL-Phosphoric Acid Catalyzed Enantioselective Hydroamination/N-Sulfonyliminium Cyclization Cascade [J].

Gregory, Alex W. ;

Jakubec, Pavol ;

Turner, Paul ;

Dixon, Darren J. .

ORGANIC LETTERS, 2013, 15 (17) :4330-4333

[3] ELECTROPHILIC SUBSTITUTION IN INDOLES .2. FORMATION OF 3,3-SPIROCYCLIC INDOLE DERIVATIVES FROM TRYPTAMINES AND THEIR REARRAGNEMENT TO BETA-CARBOLINES [J].

JACKSON, AH ;

SMITH, AE .

TETRAHEDRON, 1968, 24 (01) :403-&

[4] Synthesis of Spirocyclic Indolenines [J].

James, Michael J. ;

O'Brien, Peter ;

Taylor, Richard J. K. ;

Unsworth, William P. .

CHEMISTRY-A EUROPEAN JOURNAL, 2016, 22 (09) :2856-2881

[5] On the formation of isochinolin-derivatives through the development of methylial on phenyl-aether, phenyl-alanin and tyrosin. [J].

Pictet, A ;

Spengler, T .

BERICHTE DER DEUTSCHEN CHEMISCHEN GESELLSCHAFT, 1911, 44 :2030-2036

[6] Catalytic asymmetric Pictet-Spengler reaction [J].

Seayad, J ;

Seayad, AM ;

List, B .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (04) :1086-1087

[7] Highly enantioselective catalytic acyl-Pictet-Spengler reactions [J].

Taylor, MS ;

Jacobsen, EN .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (34) :10558-10559

[8] Catalytic asymmetric Pictet-Spengler reactions via sulfenyliminium ions [J].

Wanner, Martin J. ;

van der Haas, Richard N. S. ;

de Cuba, Kimberly R. ;

van Maarseveen, Jan H. ;

Hiemstra, Henk .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (39) :7485-7487

[9] Unified Mechanistic Understandings of Pictet-Spengler Reactions [J].

Zheng, Chao ;

Xia, Zi-Lei ;

You, Shu-Li .

CHEM, 2018, 4 (08) :1952-1966

[10] Catalytic Asymmetric Dearomatization by Transition-Metal Catalysis: A Method for Transformations of Aromatic Compounds [J].

Zheng, Chao ;

You, Shu-Li .

CHEM, 2016, 1 (06) :830-857

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