Palladium-Mediated Phosphine-Dependent Chemoselective Bisallylic Alkylation Leading to Spirocarbocycles

被引：26

作者：

Clavier, Herve ^{[1
]}

Giordano, Laurent ^{[1
]}

Tenaglia, Alphonse ^{[1
]}

机构：

[1] Aix Marseille Univ, Equipe Chirosci, Ecole Cent Marseille, UMR CNRS iSm2 7313, F-13397 Marseille 20, France

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2012年 / 51卷 / 34期

关键词：

allylic substitution; C?C activation; palladium; phosphines; spiro compounds; ASYMMETRIC ALLYLIC ALKYLATION; C-C; CATALYZED TANDEM; SUBSTITUTION; BACILLARIOLIDES; LIGANDS; ACETALS;

D O I：

10.1002/anie.201204629

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Cycles everywhere: The selectivity in the transformations of 1,3-diones to carbocycles by palladium-catalyzed bisallylic alkylations is strongly dependent on the phosphine that is employed (see scheme). Moreover, synthesized vinylcyclopentenes can be easily transformed into cycloheptadiene derivatives through a carboncarbon allylic bond cleavage.

引用

页码：8648 / 8651

页数：4

共 47 条

[1]

Achard T., 2011, ANGEW CHEM, V123, P3614

[2] A Regio- and Diastereoselective Platinum-Catalyzed Tandem [2+1]/[3+2] Cycloaddition Sequence [J].

Achard, Thierry ;

Lepronier, Aymeric ;

Gimbert, Yves ;

Clavier, Herve ;

Giordano, Laurent ;

Tenaglia, Alphonse ;

Buono, Gerard .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (15) :3552-3556

[3] Further developments in metal-catalysed C-C bond cleavage in allylic dimethyl malonate derivatives [J].

Bricout, H ;

Carpentier, JF ;

Mortreux, A .

TETRAHEDRON LETTERS, 1997, 38 (06) :1053-1056

[4] Expeditious formation of γ-lactones upon palladium-catalyzed double nucleophilic addition of bis(TMS)ketene acetals to vicinal allylacetates [J].

Chavez, Cesar Sandoval ;

Rudler, Henri ;

Parlier, Andree ;

Herson, Patrick .

TETRAHEDRON LETTERS, 2008, 49 (41) :5843-5846

[5] Highly Selective Cobalt-Mediated [6+2] Cycloaddition of Cycloheptatriene and Allenes [J].

Clavier, Herve ;

Le Jeune, Karel ;

de Riggi, Innocenzo ;

Tenaglia, Alphonse ;

Buono, Gerard .

ORGANIC LETTERS, 2011, 13 (02) :308-311

[6] Leaving Group Potential of a Substituted Cyclopentadienyl Anion Toward Oxidative Addition [J].

Fisher, Ethan L. ;

Lambert, Tristan H. .

ORGANIC LETTERS, 2009, 11 (18) :4108-4110

[7] REGIOSELECTIVE AND STEREOSELECTIVE PALLADIUM CATALYZED AMINATION OF ALLYLIC SUBSTRATES - SYNTHESIS OF E-4-AMINO-2-ALKEN-1-OL DERIVATIVES [J].

GENET, JP ;

BALABANE, M ;

BACKVALL, JE ;

NYSTROM, JE .

TETRAHEDRON LETTERS, 1983, 24 (27) :2745-2748

[8] Stereodivergent approach to the asymmetric synthesis of bacillariolides:: A formal synthesis of ent-bacillariolide II [J].

Ghosh, Subrata ;

Sinha, Saikat ;

Drew, Michael G. B. .

ORGANIC LETTERS, 2006, 8 (17) :3781-3784

[9] Palladium-catalyzed asymmetric tandem allylic substitution using chiral 2-(phosphinophenyl)pyridine ligand [J].

Ito, K ;

Imahayashi, Y ;

Kuroda, T ;

Eno, S ;

Saito, B ;

Katsuki, T .

TETRAHEDRON LETTERS, 2004, 45 (39) :7277-7281

[10] Allylic amination [J].

Johannsen, M ;

Jorgensen, KA .

CHEMICAL REVIEWS, 1998, 98 (04) :1689-1708

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