Cooperative Organocatalysis for the Asymmetric γ Alkylation of α-Branched Enals

被引：196

作者：

Bergonzini, Giulia ^{[2
]}

Vera, Silvia ^{[2
]}

Melchiorre, Paolo ^{[1
,2
]}

机构：

[1] Passeig Lluis Co 23, ICREA, Barcelona 08010, Spain

[2] ICIQ Inst Chem Res Catalonia, Tarragona 43007, Spain

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2010年 / 49卷 / 50期

关键词：

alkylation; asymmetric catalysis; dienamines; organocatalysis; vinylogous reaction; CATALYSIS; ALDEHYDES; ANNULATION;

D O I：

10.1002/anie.201004761

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

α Branched leads to γ: The direct and enantioselective γ alkylation of α-substituted α,β-unsaturated aldehydes under dienamine catalysis has been achieved. A cooperative catalysis system that involves dienamine activation of α-branched enals and chiral Brønsted acid catalysis promotes an SN1-alkylation pathway while ensuring complete γ-site selectivity and high stereocontrol (see scheme; Bn=benzyl). Copyright © 2010 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

引用

页码：9685 / 9688

页数：4

共 50 条

[1] Stronger bronsted acids
Akiyama, Takahiko
[J]. CHEMICAL REVIEWS, 2007, 107 (12) : 5744 - 5758
[2] [Anonymous], 2005, Angew. Chem
[3] Organocatalytic Activity of Cinchona Alkaloids: Which Nitrogen Is More Nucleophilic?
Baidya, Mahiuddin
Horn, Markus
Zipse, Hendrik
Mayr, Herbert
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2009, 74 (18) : 7157 - 7164
[4] A novel organocatalytic tool for the iminium activation of α,β-unsaturated ketones
Bartoli, Giuseppe
Melchiorre, Paolo
[J]. SYNLETT, 2008, (12) : 1759 - 1772
[5] Direct asymmetric vinylogous Michael addition of cyclic enones to nitroalkenes via dienamine catalysis
Bencivenni, Giorgio
Galzerano, Patrizia
Mazzanti, Andrea
Bartoli, Giuseppe
Melchiorre, Paolo
[J]. PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 2010, 107 (48) : 20642 - 20647
[6] Dienamine catalysis:: Organocatalytic asymmetric γ-amination of α,β unsaturated aldehydes
Bertelsen, Slren
Marigo, Mauro
Brandes, Sebastian
Diner, Peter
Jorgensen, Karl Anker
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (39) : 12973 - 12980
[7] Enantioselective Catalytic α-Alkylation of Aldehydes via an SN1 Pathway
Brown, Adam R.
Kuo, Wen-Hsin
Jacobsen, Eric N.
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (27) : 9286 - 9288
[8] The first enantioselective organocatalytic Mukaiyama- Michael reaction:: A direct method for the synthesis of enantioenriched γ-butenolide architecture
Brown, SP
Goodwin, NC
MacMillan, DWC
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (05) : 1192 - 1194
[9] Cooperative N-Heterocyclic Carbene/Lewis Acid Catalysis for Highly Stereoselective Annulation Reactions with Homoenolates
Cardinal-David, Benoit
Raup, Dustin E. A.
Scheidt, Karl A.
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (15) : 5345 - +
[10] The vinylogous aldol reaction: A valuable, yet understated carbon-carbon bond-forming maneuver
Casiraghi, G
Zanardi, F
Appendino, G
Rassu, G
[J]. CHEMICAL REVIEWS, 2000, 100 (06) : 1929 - 1972

← 1 2 3 4 5 →