Organocatalytic highly enantioselective α-arylation of β-ketoesters

被引：93

作者：

Aleman, Jose ^{[1
]}

Richter, Bo ^{[1
]}

Jorgensen, Karl Anker ^{[1
]}

机构：

[1] Aarhus Univ, Danish Natl Res Fdn, Ctr Catalysis Dept Chem, DK-8000 Aarhus C, Denmark

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2007年 / 46卷 / 29期

关键词：

alpha-arylation; beta-ketoesters; organcatalysis; quinine; quinones;

D O I：

10.1002/anie.200701009

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Quintessential quinones: The reaction of β-ketoesters with quinones provides a strategy to perform α-arylations, particularly when the α-aryl ring contains electron-donating groups. The reaction can be carried out enantioselectively by using cinchona alkaloids as organocatalysts and allows the synthesis of complicated polycyclic and spiro chiral compounds. (Figure Presented) © 2007 Wiley-VCH Verlag GmbH & Co. KGaA.

引用

页码：5515 / 5519

页数：5

共 43 条

[1] [Anonymous], ACC CHEM RES
[2] [Anonymous], 2006, ANGEW CHEM, V118, P1550
[3] Organocatalytic asymmetric α-halogenation of 1,3-dicarbonyl compounds
Bartoli, G
Bosco, M
Carlone, A
Locatelli, M
Melchiorre, P
Sambri, L
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (38) : 6219 - 6222
[4] Bartoli G, 2006, ANGEW CHEM, V118, P5088, DOI DOI 10.1002/ange.200600370
[5] Bartoli G., 2005, ANGEW CHEM, V117, P6375
[6] Organocatalytic asymmetric conjugate addition of 1,3-dicarbonyl compounds to maleimides
Bartoli, Giuseppe
Bosco, Marcella
Carlone, Armando
Cavalli, Andrea
Locatelli, Manuela
Mazzanti, Andrea
Ricci, Paolo
Sambri, Letizia
Melchiorre, Paolo
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (30) : 4966 - 4970
[7] Organocatalytic regio- and asymmetric C-selective SNAr reactions-stereoselective synthesis of optically active spiro-pyrrolidone-3,3′-oxoindoles
Bella, M
Kobbelgaard, S
Jorgensen, KA
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (11) : 3670 - 3671
[8] Berkessel A, 2005, ASYMMETRIC ORGANOCATALYSIS: FROM BIOMIMETIC CONCEPTS TO APPLICATIONS IN ASYMMETRIC SYNTHESIS, P1, DOI 10.1002/3527604677
[9] RATIONALIZING THE REGIOSELECTIVITY IN POLYNITROARENE ANIONIC SIGMA-ADDUCT FORMATION - RELEVANCE TO NUCLEOPHILIC AROMATIC-SUBSTITUTION
BUNCEL, E
DUST, JM
TERRIER, F
[J]. CHEMICAL REVIEWS, 1995, 95 (07) : 2261 - 2280
[10] CHRISTOFFERS J, 1999, EUR J ORG CHEM, P1259

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