Ligand-Controlled Iron-Catalyzed Coupling of α-Substituted β-Ketoesters with Phenols

被引：56

作者：

Parnes, Regev ^{[1
]}

Kshirsagar, Umesh A. ^{[1
]}

Werbeloff, Aviya ^{[1
]}

Regev, Clil ^{[1
]}

Pappo, Doron ^{[1
]}

机构：

[1] Ben Gurion Univ Negev, Dept Chem, IL-84105 Beer Sheva, Israel

来源：

ORGANIC LETTERS | 2012年 / 14卷 / 13期

基金：

以色列科学基金会;

关键词：

C-H BONDS; TERTIARY-AMINES; NITROGEN ATOM; ALKYNYLATION; DERIVATIVES; ALDEHYDES; ADJACENT; 2-NAPHTHOLS; ALKYLATION; ACTIVATION;

D O I：

10.1021/ol301297k

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A chemo-, regio-, and stereoselective FeCl3/1,10-phenanthroline-catalyzed cross dehydrogenative coupling (CDC) reaction between phenols and alpha-substituted beta-ketoesters was developed. The reaction creates a new quaternary carbon center within a polycyclic hemiacetal or polycyclic spirolactone architecture. The applicability of the new method to the synthesis of natural products was demonstrated by a possible biomimetic synthesis of the lachnanthospirone core.

引用

页码：3324 / 3327

页数：4

共 43 条

[1] Organocatalytic highly enantioselective α-arylation of β-ketoesters [J].

Aleman, Jose ;

Richter, Bo ;

Jorgensen, Karl Anker .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (29) :5515-5519

[2] THE SYNTHESIS OF USNIC ACID [J].

BARTON, DHR ;

DEFLORIN, AM ;

EDWARDS, OE .

JOURNAL OF THE CHEMICAL SOCIETY, 1956, (MAR) :530-534

[3] Directed Oxidative Cyclizations to C2- or C4-Positions of Indole: Efficient Construction of the Bicyclo[4.3.1]Decane Core of Welwitindolinones [J].

Bhat, Vikram ;

MacKay, James A. ;

Rawal, Viresh H. .

ORGANIC LETTERS, 2011, 13 (12) :3214-3217

[4] The Copper-Catalyzed Decarboxylative Coupling of the sp3-Hybridized Carbon Atoms of α-Amino Acids [J].

Bi, Hai-Peng ;

Zhao, Liang ;

Liang, Yong-Min ;

Li, Chao-Jun .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (04) :792-795

[5] MANGANESE(III) ACETATE INDUCED CYCLIZATION OF ALPHA-ARYLALKYL AND ALPHA-(ARYLOXY)ALKYL BETA-DICARBONYL DERIVATIVES [J].

CITTERIO, A ;

FANCELLI, D ;

FINZI, C ;

PESCE, L ;

SANTI, R .

JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (11) :2713-2718

[6] Intermolecular enolate heterocoupling: Scope, mechanism, and application [J].

DeMartino, Michael P. ;

Chen, Ke ;

Baran, Phil S. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (34) :11546-11560

[7]

Edwards J.M., 1979, TETRAHEDRON LETT, V20, P4453

[8] Enantioenriched Synthesis of C1-Symmetric BINOLs: Iron-Catalyzed Cross-Coupling of 2-Naphthols and Some Mechanistic Insight [J].

Egami, Hiromichi ;

Matsumoto, Kenji ;

Oguma, Takuya ;

Kunisu, Takashi ;

Katsuki, Tsutomu .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (39) :13633-13635

[9] Iron-Catalyzed Asymmetric Aerobic Oxidation: Oxidative Coupling of 2-Naphthols [J].

Egami, Hiromichi ;

Katsuki, Tsutomu .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2009, 131 (17) :6082-+

[10] Total Synthesis of (±) Maoecrystal V [J].

Gong, Jianxian ;

Lin, Guang ;

Sun, Wenbo ;

Li, Chuang-Chuang ;

Yang, Zhen .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (47) :16745-16746

← 1 2 3 4 5 →