Highly enantioselective synthesis of tetrahydro-β-carbolines and tetrahydro-γ-carbolines via Pd-catalyzed intramolecular allylic alkylation

被引：175

作者：

Bandini, M ^{[1
]}

Melloni, A ^{[1
]}

Piccinelli, F ^{[1
]}

Sinisi, R ^{[1
]}

Tommasi, S ^{[1
]}

Umani-Ronchi, A ^{[1
]}

机构：

[1] Univ Bologna, Dipartimento Chim G Ciamician, Alma Mater Studiorum, I-40126 Bologna, Italy

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2006年 / 128卷 / 05期

关键词：

D O I：

10.1021/ja054109o

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A novel Pd-catalyzed intramolecular allylic alkylation of indoles allows THBCs and THGCs to be effectively synthesized in high yields and excellent enantiomeric excesses (ee up to 97%). Copyright © 2006 American Chemical Society.

引用

页码：1424 / 1425

页数：2

共 23 条

[1] [Anonymous], 1981, INTRO ALKALOIDS, DOI DOI 10.1002/JPS.2600720334
[2] A journey across recent advances in catalytic and stereoselective alkylation of indoles
Bandini, M
Melloni, A
Tommasi, S
Umani-Ronchi, A
[J]. SYNLETT, 2005, (08) : 1199 - 1222
[3] New versatile Pd-catalyzed alkylation of indoles via nucleophilic allylic subsitution: Controlling the regioselectivity
Bandini, M
Melloni, A
Umani-Ronchi, A
[J]. ORGANIC LETTERS, 2004, 6 (18) : 3199 - 3202
[4] New catalytic approaches in the stereoselective Friedel-Crafts alkylation reaction
Bandini, M
Melloni, A
Umani-Ronchi, A
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (05) : 550 - 556
[5] Synthesis and evaluation of analogues of the partial agonist 6-(propyloxy)-4-(methoxymethyl)-β-carboline-3-carboxylic acid ethyl ester (6-PBC) and the full agonist 6-(benzyloxy)-4-(methoxymethyl)-β-carboline-3-carboxylic acid ethyl ester (Zk 93423) at wild type and recombinant GABAA receptors
Cox, ED
Diaz-Arauzo, H
Huang, Q
Reddy, MS
Ma, CR
Harris, B
McKernan, R
Skolnick, P
Cook, JM
[J]. JOURNAL OF MEDICINAL CHEMISTRY, 1998, 41 (14) : 2537 - 2552
[6] THE PICTET-SPENGLER CONDENSATION - A NEW DIRECTION FOR AN OLD REACTION
COX, ED
COOK, JM
[J]. CHEMICAL REVIEWS, 1995, 95 (06) : 1797 - 1842
[7] Enantiopure tetrahydro-β-carbolines via Pictet-Spengler reactions with N-sulfinyl tryptamines
Gremmen, C
Willemse, B
Wanner, MJ
Koomen, GJ
[J]. ORGANIC LETTERS, 2000, 2 (13) : 1955 - 1958
[8] Phosphinooxazolines - A new class of versatile, modular P,N-ligands for asymmetric catalysis
Helmchen, G
Pfaltz, A
[J]. ACCOUNTS OF CHEMICAL RESEARCH, 2000, 33 (06) : 336 - 345
[9] MULTIMACROCYCLIC COMPOUNDS .4. INTERNAL TRIMERISATION OF TRIPLE BONDS OF LINEAR TRIYNES ON A ZIEGLER CATALYST
HUBERT, AJ
[J]. JOURNAL OF THE CHEMICAL SOCIETY C-ORGANIC, 1967, (20): : 1984 - &
[10] Binding of tetrahydrocarboline derivatives at human 5-HT5A receptors
Khorana, N
Smith, C
Herrick-Davis, K
Purohit, A
Teitler, M
Grella, B
Dukat, M
Glennon, RA
[J]. JOURNAL OF MEDICINAL CHEMISTRY, 2003, 46 (18) : 3930 - 3937

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