Asymmetric Organocatalytic Cascade Reactions with α-Substituted α,β-Unsaturated Aldehydes

被引：131

作者：

Galzerano, Patrizia ^{[1
]}

Pesciaioli, Fabio ^{[1
]}

Mazzanti, Andrea ^{[1
]}

Bartoli, Giuseppe ^{[1
]}

Melchiorre, Paolo ^{[1
,2
]}

机构：

[1] Univ Bologna, Dipartimento Chim Organ A Mangini, I-40136 Bologna, Italy

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

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2009年 / 48卷 / 42期

关键词：

aldehydes; cascade reactions; molecular complexity; organocatalysis; quaternary stereocenters; CHIRAL PRIMARY AMINE; IMINIUM ACTIVATION; DOMINO REACTIONS; CATALYSIS; KETONES; ENONES; AMINOCATALYSIS; STEREOCENTERS; ALKYLATION; CHEMISTRY;

D O I：

10.1002/anie.200903803

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Time to α-branch out! The first highly enantioselective aminocatalytic activation of a-substituted αβ-unsaturated aldehydes is presented. The chiral primary amine 1 selectively activates ct-branched enals toward a well-defined iminium ion enamine reaction sequence for both Friedel-Crafts/amination and sulfa-Michael/ amination cascades. The valuable multifunctional products, having two contiguous sterocenters, are isolated in high enantiomeric purity. © 2009 Wiley-VCH Verlag GmbH & Co. KGaA.

引用

页码：7892 / 7894

页数：3

共 41 条

[31] Cascade reactions in total synthesis [J].

Nicolaou, K. C. ;

Edmonds, David J. ;

Bulger, Paul G. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (43) :7134-7186

[32]

Pesciaioli F., 2008, ANGEW CHEM, V120, P8831

[33] Organocatalytic Asymmetric Aziridination of Enones [J].

Pesciaioli, Fabio ;

De Vincentiis, Francesco ;

Galzerano, Patrizia ;

Bencivenni, Giorgio ;

Bartoli, Giuseppe ;

Mazzanti, Andrea ;

Melchiorre, Paolo .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (45) :8703-8706

[34]

Sibi M. P., 2008, ANGEW CHEM, V120, P10061

[35] Enantioselective Enolate Protonations: Friedel-Crafts Reactions with α-Substituted Acrylates [J].

Sibi, Mukund P. ;

Coulomb, Julien ;

Stanley, Levi M. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (51) :9913-9915

[36] Cycle-Specific Organocascade Catalysis: Application to Olefin Hydroamination, Hydro-oxidation, and Amino-oxidation, and to Natural Product Synthesis [J].

Simmons, Bryon ;

Walji, Abbas M. ;

MacMillan, David W. C. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (24) :4349-4353

[37] NEW METHOD FOR MAXIMIZING OPTICAL PURITY OF PARTIALLY REDUPLICATED PRODUCT WITHOUT USING CHIRAL SUBSTANCE [J].

VIGNERON, JP ;

DHAENENS, M ;

HOREAU, A .

TETRAHEDRON, 1973, 29 (07) :1055-1059

[38] Catalytic asymmetric epoxidation of cyclic enones [J].

Wang, Xingwang ;

Reisinger, Corinna M. ;

List, Benjamin .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (19) :6070-+

[39] Organocascade Reactions of Enones Catalyzed by a Chiral Primary Amine [J].

Wu, Li-Yuan ;

Bencivenni, Giorgio ;

Mancinelli, Michele ;

Mazzanti, Andrea ;

Bartoli, Giuseppe ;

Melchiorre, Paolo .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (39) :7196-7199

[40]

WU LY, 2009, ANGEW CHEM, V121, P7329

← 1 2 3 4 5 →