Organocatalytic Asymmetric Alkylation of Aldehydes by SN1-Type Reaction of Alcohols

被引：234

作者：

Cozzi, Pier Giorgio ^{[1
]}

Benfatti, Fides ^{[1
]}

Zoli, Luca ^{[1
]}

机构：

[1] Univ Bologna, Dipartimento Chim G Ciamician, ALMA MATER STUDIORUM, I-40126 Bologna, Italy

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2009年 / 48卷 / 07期

关键词：

alcohols; aldehydes; carbocations; enamines; organocatalysis; NUCLEOPHILIC-SUBSTITUTION; PROPARGYLIC ALCOHOLS; ORGANIC CATALYSIS; ALPHA-ALKYLATION; BENZYLATION; INDOLES; CYCLOPROPANES; REACTIVITIES; ENHANCEMENT; CHEMISTRY;

D O I：

10.1002/anie.200805423

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Work-alcoholic! The elusive enantioselective catalytic α-alkylation of aldehydes, a widely sought transformation, was brought to execution by the use of alcohols capable of forming stabilized carbocations (see scheme, TFA=trifluoroacetic acid). © 2009 Wiley-VCH Verleg GmbH & Co. KGaA.

引用

页码：1313 / 1316

页数：4

共 82 条

[1] Organocatalytic reactions with acetaldehyde [J].

Alcaide, Benito ;

Almendros, Pedro .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (25) :4632-4634

[2]

Almendros P., 2008, ANGEW CHEM, V120, P4710

[3]

[Anonymous], 2008, ANGEW CHEM

[4]

[Anonymous], 2004, Angew. Chem, V116, P5248, DOI DOI 10.1002/ANGE.200400650

[5] Reaction of 3-(1-arylsulfonylalkyl)-indoles with easily enolisable derivatives promoted by potassium fluoride on basic alumina [J].

Ballini, Roberto ;

Palmieri, Alessandro ;

Petrini, Marino ;

Shaikh, Rafik R. .

ADVANCED SYNTHESIS & CATALYSIS, 2008, 350 (01) :129-134

[6] Solventless clay-promoted Friedel-Crafts reaction of indoles with α-amido sulfones:: Unexpected synthesis of 3-(1-arylsulfonylalkyl) indoles [J].

Ballini, Roberto ;

Palmieri, Alessandro ;

Petrini, Marino ;

Torregiani, Elisabetta .

ORGANIC LETTERS, 2006, 8 (18) :4093-4096

[7] Organocatalysis - Organocatalysis lost: Modern chemistry, ancient chemistry, and an unseen biosynthetic apparatus [J].

Barbas, Carlos F., III .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (01) :42-47

[8] Enantioselective organocatalysis using SOMO activation [J].

Beeson, Teresa D. ;

Mastracchio, Anthony ;

Hong, Jun-Bae ;

Ashton, Kate ;

MacMillan, David W. C. .

SCIENCE, 2007, 316 (5824) :582-585

[9]

Berkessel A, 2005, ASYMMETRIC ORGANOCATALYSIS: FROM BIOMIMETIC CONCEPTS TO APPLICATIONS IN ASYMMETRIC SYNTHESIS, P1, DOI 10.1002/3527604677

[10]

Blackmond D.G., 2007, ANGEW CHEM, V119, P3872

← 1 2 3 4 5 6 7 8 9 →