Catalytic Asymmetric Cyclopropanation with Diazooxindole

被引：53

作者：

Awata, Atsuko ^{[1
]}

Arai, Takayoshi ^{[1
]}

机构：

[1] Chiba Univ, Grad Sch Sci, Dept Chem, Inage Ku, Chiba 2638522, Japan

来源：

SYNLETT | 2013年 / 24卷 / 01期

关键词：

asymmetric catalysis; spiro compounds; carbenoids; cyclopropanation; oxindole; HIGHLY ENANTIOSELECTIVE CYCLOPROPANATION; REVERSE-TRANSCRIPTASE INHIBITORS; SUBSTITUTED RHODIUM CARBENOIDS; BRYOZOAN AMATHIA-CONVOLUTA; ELECTRON-DEFICIENT OLEFINS; STRUCTURE-BASED DESIGN; H INSERTION REACTIONS; MAMMALIAN-CELL CYCLE; DIASTEREOSELECTIVE SYNTHESIS; CHIRAL LIGANDS;

D O I：

10.1055/s-0032-1317746

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The first catalytic asymmetric cyclopropanation using styrene and diazooxindole was achieved with Rh-2(S-PTTL)(4). The reaction proceeded smoothly with 1 mol% catalyst loading to provide a good yield of the biologically important spiro-cyclopropyloxindole product with moderate to good enantioselectivity and excellent diastereoselectivity.

引用

页码：29 / 32

页数：4

共 83 条

[1] Asymmetric Inter- and Intramolecular Cyclopropanation Reactions Catalyzed by a Reusable Macroporous-Polymer-Supported Chiral Ruthenium(II)/Phenyloxazoline Complex [J].

Abu-Elfotoh, Abdel-Moneim ;

Phomkeona, Kesiny ;

Shibatomi, Kazutaka ;

Iwasa, Seiji .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2010, 49 (45) :8439-8443

[2]

[Anonymous], 2007, ANGEW CHEM, DOI DOI 10.1103/PHYSREVLETT.112.077206

[3] Catalytic Asymmetric exo'-Selective [3+2] Cycloaddition for Constructing Stereochemically Diversified Spiro[pyrrolidin-3,3'-oxindole]s [J].

Awata, Atsuko ;

Arai, Takayoshi .

CHEMISTRY-A EUROPEAN JOURNAL, 2012, 18 (27) :8278-8282

[4] Enantioselective total syntheses of welwitindolinone A and fischerindoles I and G [J].

Baran, PS ;

Richter, JM .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (44) :15394-15396

[5]

Bindra J.S., 1973, The Alkaloids, V14, P84

[6] Rh(II) catalysts with 4-hydroxyproline-derived ligands [J].

Bonge, Hanne Therese ;

Kaboli, Massoud ;

Hansen, Tore .

TETRAHEDRON LETTERS, 2010, 51 (41) :5375-5377

[7] Palladium-catalyzed cyclopropanation of electron-deficient olefins with aryldiazocarbonyl compounds [J].

Chen, Shufeng ;

Ma, Jian ;

Wang, Jianbo .

TETRAHEDRON LETTERS, 2008, 49 (48) :6781-6783

[8] Cobalt-catalyzed asymmetric cyclopropanation of electron-deficient olefins [J].

Chen, Ying ;

Ruppel, Joshua V. ;

Zhang, X. Peter .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (40) :12074-+

[9] Asymmetric cyclopropanation of styrenes catalyzed by metal complexes of D2-Symmetrical chiral porphyrin:: Superiority of cobalt over iron [J].

Chen, Ying ;

Zhang, X. Peter .

JOURNAL OF ORGANIC CHEMISTRY, 2007, 72 (15) :5931-5934

[10] Spirotryprostatin B, a novel mammalian cell cycle inhibitor produced by Aspergillus fumigatus [J].

Cui, CB ;

Kakeya, H ;

Osada, H .

JOURNAL OF ANTIBIOTICS, 1996, 49 (08) :832-835

← 1 2 3 4 5 6 7 8 9 →