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

[11] Novel mammalian cell cycle inhibitors, spirotryprostatins A and B, produced by Aspergillus fumigatus, which inhibit mammalian cell cycle at G2/M phase [J].

Cui, CB ;

Kakeya, H ;

Osada, H .

TETRAHEDRON, 1996, 52 (39) :12651-12666

[12]

Dandia A, 2002, PHARMAZIE, V57, P602

[13] Stereoselectivity of methyl aryldiazoacetate cyclopropanations of 1,1-diarylethylene. Asymmetric synthesis of a cyclopropyl analogue of tamoxifen [J].

Davies, HML ;

Nagashima, T ;

Klino, JL .

ORGANIC LETTERS, 2000, 2 (06) :823-826

[14] Asymmetric cyclopropanations by rhodium(II) N-(arylsulfonyl)prolinate catalyzed decomposition of vinyldiazomethanes in the presence of alkenes. Practical enantioselective synthesis of the four stereoisomers of 2-phenylcyclopropan-1-amino acid [J].

Davies, HML ;

Bruzinski, PR ;

Lake, DH ;

Kong, N ;

Fall, MJ .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (29) :6897-6907

[15] Dirhodium tetraprolinate-catalyzed asymmetric cycloproplanations with high turnover numbers [J].

Davies, HML ;

Venkataramani, C .

ORGANIC LETTERS, 2003, 5 (09) :1403-1406

[16] Catalytic asymmetric cyclopropanation of heteroaryldiazoacetates [J].

Davies, HML ;

Townsend, RJ .

JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (20) :6595-6603

[17] Effect of diazoalkane structure on the stereoselectivity of rhodium(II) (S)-N-(arylsulfonyl)prolinate catalyzed cyclopropanations [J].

Davies, HML ;

Bruzinski, PR ;

Fall, MJ .

TETRAHEDRON LETTERS, 1996, 37 (24) :4133-4136

[18] Chiral Crown Conformation of Rh2(S-PTTL)4: Enantioselective Cyclopropa nation with α-Alkyl-α-diazoesters [J].

DeAngelis, Andrew ;

Dmitrenko, Olga ;

Yap, Glenn P. A. ;

Fox, Joseph M. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2009, 131 (21) :7230-+

[19] Structure-based design of potent non-peptide MDM2 inhibitors [J].

Ding, K ;

Lu, Y ;

Nikolovska-Coleska, Z ;

Qiu, S ;

Ding, YS ;

Gao, W ;

Stuckey, J ;

Krajewski, K ;

Roller, PP ;

Tomita, Y ;

Parrish, DA ;

Deschamps, JR ;

Wang, SM .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (29) :10130-10131

[20] Structure-based design of spiro-oxindoles as potent, specific small-molecule inhibitors of the MDM2-p53 interaction [J].

Ding, Ke ;

Lu, Yipin ;

Nikolovska-Coleska, Zaneta ;

Wang, Guoping ;

Qiu, Su ;

Shangary, Sanjeev ;

Gao, Wei ;

Qin, Dongguang ;

Stuckey, Jeanne ;

Krajewski, Krzysztof ;

Roller, Peter P. ;

Wang, Shaomeng .

JOURNAL OF MEDICINAL CHEMISTRY, 2006, 49 (12) :3432-3435

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