B(C6F5)3-catalyzed cyclopropanation of 3-alkenyl-oxindoles with diazomethanes

被引：19

作者：

Xiao, Lei ^{[1
]}

Jin, Lvnan ^{[1
]}

Zhao, Yunbo ^{[1
]}

Guo, Jing ^{[1
]}

Stephan, Douglas W. W. ^{[1
,2
]}

机构：

[1] Ningbo Univ, Inst Drug Discovery Technol, Ningbo, Zhejiang, Peoples R China

[2] Univ Toronto, Dept Chem, 80 St George St, Toronto, ON M5S 3H6, Canada

来源：

CHEMICAL COMMUNICATIONS | 2023年 / 59卷 / 13期

关键词：

REVERSE-TRANSCRIPTASE INHIBITORS; H BOND FUNCTIONALIZATION; DIAZO-COMPOUNDS; ASYMMETRIC CYCLOPROPANATION; BIOLOGICAL EVALUATIONS; INSERTION; PHENOLS; DIAZOOXINDOLES; OXINDOLES; DESIGN;

D O I：

10.1039/d2cc06744g

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Spirocyclopropane-oxindoles are key motifs in biologically active compounds and are versatile synthetic intermediates. Herein, we report a metal-free, B(C6F5)(3) catalyzed cyclopropanation of 3-alkenyl-oxindoles with diazomethanes. This provides 25 variants of spirocyclopropane-oxindole derivatives. These spirocyclopropane-oxindole products were obtained in good to excellent yields (up to 99%) and high diastereoselectivities (up to 20 : 1 d.r.) under mild reaction conditions and could be performed on a gram scale.

引用

页码：1833 / 1836

页数：4

共 50 条

[21]

Jiang T, 2006, BIOORG MED CHEM LETT, V16, P2105, DOI 10.1016/j.bmcl.2006.01.073

[22] Catalyst-dependent chemoselective insertion of diazoalkanes into the N-H/C-H/O-H/C-O bonds of 2-hydroxybenzothiazoles [J].

Jin, Lvnan ;

Zhou, Xuan ;

Zhao, Yunbo ;

Guo, Jing ;

Stephan, Douglas W. .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2022, 20 (39) :7781-+

[23] Rhodium(II) acetate-catalyzed stereoselective synthesis, SAR and anti-HIV activity of novel oxindoles bearing cyclopropane ring [J].

Kumari, Garima ;

Nutan ;

Modi, Manoj ;

Gupta, Satish K. ;

Singh, Ramendra K. .

EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2011, 46 (04) :1181-1188

[24] Rh(II)-Catalyzed Cyclopropanation of Furans and Its Application to the Total Synthesis of Natural Product Derivatives [J].

Lehner, Verena ;

Davies, Huw M. L. ;

Reiser, Oliver .

ORGANIC LETTERS, 2017, 19 (18) :4722-4725

[25] Carbene transfer reactions between transition-metal ions [J].

Liu, ST ;

Reddy, KR .

CHEMICAL SOCIETY REVIEWS, 1999, 28 (05) :315-322

[26] Origins of unique gold-catalysed chemo- and site-selective C-H functionalization of phenols with diazo compounds [J].

Liu, Yuan ;

Yu, Zhunzhun ;

Zhang, John Zenghui ;

Liu, Lu ;

Xia, Fei ;

Zhang, Junliang .

CHEMICAL SCIENCE, 2016, 7 (03) :1988-1995

[27] Copper-catalysedortho-selective C-H bond functionalization of phenols and naphthols with α-aryl-α-diazoesters [J].

Ma, Ben ;

Tang, Zhiqiong ;

Zhang, Junliang ;

Liu, Lu .

CHEMICAL COMMUNICATIONS, 2020, 56 (66) :9485-9488

[28] Tris(pentafluorophenyl)borane-Catalyzed Cyclopropanation of Styrenes with Aryldiazoacetates [J].

Mancinelli, Joseph P. ;

Wilkerson-Hill, Sidney M. .

ACS CATALYSIS, 2020, 10 (19) :11171-11176

[29] Tridentate Nickel(II)-Catalyzed Chemodivergent C-H Functionalization and Cyclopropanation: Regioselective and Diastereoselective Access to Substituted Aromatic Heterocycles [J].

Nag, Ekta ;

Gorantla, Sai Manoj N. V. T. ;

Arumugam, Selvakumar ;

Kulkarni, Aditya ;

Mondal, Kartik Chandra ;

Roy, Sudipta .

ORGANIC LETTERS, 2020, 22 (16) :6313-6318

[30] A new vinyl selenone-based domino approach to spirocyclopropyl oxindoles endowed with anti-HIV RT activity [J].

Palomba, M. ;

Rossi, L. ;

Sancineto, L. ;

Tramontano, E. ;

Corona, A. ;

Bagnoli, L. ;

Santi, C. ;

Pannecouque, C. ;

Tabarrini, O. ;

Marini, F. .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2016, 14 (06) :2015-2024

← 1 2 3 4 5 →