An update on catalytic enantioselective alkylations of indoles

被引：20

作者：

Bandini, Marco ^{[1
]}

Eichholzer, Astrid ^{[1
]}

Umani-Ronchi, Achille ^{[1
]}

机构：

[1] Dipartimento Chim G Ciamician, I-40126 Bologna, Italy

来源：

MINI-REVIEWS IN ORGANIC CHEMISTRY | 2007年 / 4卷 / 02期

关键词：

alkylation; asymmetric catalysis; Friedel-Crafts; indoles;

D O I：

10.2174/157019307780599270

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Indole benzylic stereocenters are molecular frameworks largely present in natural occurring compounds, with their absolute configuration being of key importance in determining the biological activity of the entire molecule. In this context, the development of new catalytic asymmetric strategies for their preparation is a research area of astonishingly, rapid growth by means of organic as well as organometallic catalysts. Here, an update of this thriving scenario is presented by focusing in highly stereocontrolled Michael addition approaches, addition to carbonyl units, direct aromatic C-H activation/alkylation, and allylic alkylation.

引用

页码：115 / 124

页数：10

共 61 条

[1] A practical synthetic route to functionalized THBCs and oxygenated analogues via intramolecular Friedel-Crafts reactions
Angeli, Marco
Bandini, Marco
Garelli, Andrea
Piccinelli, Fabio
Tommasi, Simona
Umani-Ronchi, Achille
[J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2006, 4 (17) : 3291 - 3296
[2] Enantioselective organocatalytic indole alkylations. Design of a new and highly effective chiral amine for iminium catalysis
Austin, JF
MacMillan, DWC
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (07) : 1172 - 1173
[3] Highly enantioselective synthesis of tetrahydro-β-carbolines and tetrahydro-γ-carbolines via Pd-catalyzed intramolecular allylic alkylation
Bandini, M
Melloni, A
Piccinelli, F
Sinisi, R
Tommasi, S
Umani-Ronchi, A
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (05) : 1424 - 1425
[4] Catalytic enantioselective addition of indoles to arylnitroalkenes: An effective route to enantiomerically enriched tryptamine precursors
Bandini, M
Garelli, A
Rovinetti, M
Tommasi, S
Umani-Ronchi, A
[J]. CHIRALITY, 2005, 17 (09) : 522 - 529
[5] 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
[6] 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
[7] Can simple enones be useful partners for the catalytic stereoselective alkylation of indoles?
Bandini, M
Fagioli, M
Garavelli, M
Melloni, A
Trigari, V
Umani-Ronchi, A
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2004, 69 (22) : 7511 - 7518
[8] Designing new α,β-unsaturated thioesters for the catalytic, enantioselective Friedel-Crafts alkylation of indoles
Bandini, M
Melloni, A
Tommasi, S
Umani-Ronchi, A
[J]. HELVETICA CHIMICA ACTA, 2003, 86 (11) : 3753 - 3763
[9] 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
[10] Catalytic enantioselective conjugate addition of indoles to simple α,β-unsaturated ketones
Bandini, M
Fagioli, M
Melchiorre, P
Melloni, A
Umani-Ronchi, A
[J]. TETRAHEDRON LETTERS, 2003, 44 (31) : 5843 - 5846

← 1 2 3 4 5 6 7 →