Enantioselective Copper-Catalyzed Conjugate Addition of Trimethylaluminum to β,γ-Unsaturated α-Ketoamides: Efficient Access to γ-Methyl-Substituted Carbonyl Compounds

被引：25

作者：

Goncalves-Contal, Sylvie ^{[1
]}

Gremaud, Ludovic ^{[1
]}

Alexakis, Alexandre ^{[1
]}

机构：

[1] Univ Geneva, Dept Organ Chem, CH-1211 Geneva 4, Switzerland

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2013年 / 52卷 / 48期

基金：

瑞士国家科学基金会; 新加坡国家研究基金会;

关键词：

asymmetric catalysis; copper; enantioselectivity; natural products; synthetic methods; DIELS-ALDER REACTIONS; ABSOLUTE-CONFIGURATION; HYDROGENATION; COMPLEXES;

D O I：

10.1002/anie.201306541

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Picture perfect: By using the reagent trimethylaluminium and β,γ-unsaturated α-ketoamides, 1,4-adducts were obtained with perfect 1,4-regioselectivity and good to excellent yields and ee values. The potential synthetic utility of the methodology was highlighted by preparation of γ-methyl-substituted carbonyls, key synthons to many natural products. binap=2,2′-bis(diphenylphosphino)-1,1′-binaphthyl, TC=thiophene carboxylate. Copyright © 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

引用

页码：12701 / 12704

页数：4

共 31 条

[1] Enantioselective copper-catalyzed conjugate addition and allylic substitution reactions [J].

Alexakis, A. ;

Backvall, J. E. ;

Krause, N. ;

Pamies, O. ;

Dieguez, M. .

CHEMICAL REVIEWS, 2008, 108 (08) :2796-2823

[2] ORGANOCOPPER CONJUGATE ADDITION-REACTION IN THE PRESENCE OF TRIMETHYLCHLOROSILANE [J].

ALEXAKIS, A ;

BERLAN, J ;

BESACE, Y .

TETRAHEDRON LETTERS, 1986, 27 (09) :1047-1050

[3]

Alexakis A, 2002, EUR J ORG CHEM, V2002, P3221

[4] Dual Heterogeneous Catalysis for a Regioselective Three-Component Synthesis of Bi- and Tri(hetero)arylpyridines [J].

Allais, Christophe ;

Lieby-Muller, Frederic ;

Constantieux, Thierry ;

Rodriguez, Jean .

ADVANCED SYNTHESIS & CATALYSIS, 2012, 354 (13) :2537-2544

[5] Use of β,γ-Unsaturated α-Ketocarbonyls for a Totally Regioselective Oxidative Multicomponent Synthesis of Polyfunctionalized Pyridines [J].

Allais, Christophe ;

Constantieux, Thierry ;

Rodriguez, Jean .

CHEMISTRY-A EUROPEAN JOURNAL, 2009, 15 (47) :12945-12948

[6] Synthesis of 3-acetonyl- and 3-(2-oxoethyl)glutarates [J].

Amat, M ;

Bassas, O ;

Cantó, M ;

Llor, N ;

Santos, MMM ;

Bosch, J .

TETRAHEDRON, 2005, 61 (32) :7693-7702

[7]

[Anonymous], 2012, ANGEW CHEM

[8] Process-scale total synthesis of nature-identical (-)-(S,S)-7-hydroxycalamenal in high enantiomeric purity through catalytic enantioselective hydrogenation [J].

Benincori, T ;

Bruno, S ;

Celentano, G ;

Pilati, T ;

Ponti, A ;

Rizzo, S ;

Sada, M ;

Sannicolò, F .

HELVETICA CHIMICA ACTA, 2005, 88 (07) :1776-1789

[9] (+)- and (-)-Mutisianthol: First Total Synthesis, Absolute Configuration, and Antitumor Activity [J].

Bianco, Graziela G. ;

Ferraz, Helena M. C. ;

Cost, Arinice M. ;

Costa-Lotufo, Leticia V. ;

Pessoa, Claudia ;

de Moraes, Manoel O. ;

Schrems, Marcus G. ;

Pfaltz, Andreas ;

Silva, Luiz F., Jr. .

JOURNAL OF ORGANIC CHEMISTRY, 2009, 74 (06) :2561-2566

[10]

Bower, 1996, ANGEW CHEM, V108, P1662

← 1 2 3 4 →