Stereoselective synthesis 3-alkylideneoxindoles by rhodium-catalyzed cyclization reaction of 2-alkynylaryl isocyanates with aryl- and alkenylboronic acids

被引：71

作者：

Miura, Tomoya ^{[1
]}

Takahashi, Yusuke ^{[1
]}

Murakami, Masahiro ^{[1
]}

机构：

[1] Kyoto Univ, Dept Synthet Chem & Biol Chem, Katsura, Kyoto 6158510, Japan

来源：

ORGANIC LETTERS | 2007年 / 9卷 / 24期

关键词：

D O I：

10.1021/ol7024185

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The rhodium-catalyzed cyclization reaction of 2-alkynylaryl isocyanates with aryl- and alkenylboronic acids furnishes 3-alkylideneoxindoles in a stereoselective manner. The reaction allows arrangement of various substituents on the exocyclic double bond and aromatic ring with wide functional tolerance.

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页码：5075 / 5077

页数：3

相关论文

共 35 条

[31] Oxindole-based compounds are selective inhibitors of Plasmodium falciparum cyclin dependent protein kinases [J].

Woodard, CL ;

Li, ZY ;

Kathcart, AK ;

Terrell, J ;

Gerena, L ;

Lopez-Sanchez, M ;

Kyle, DE ;

Bhattacharjee, AK ;

Nichols, DA ;

Ellis, W ;

Prigge, ST ;

Geyer, JA ;

Waters, NC .

JOURNAL OF MEDICINAL CHEMISTRY, 2003, 46 (18) :3877-3882

[32] Stereoselective synthesis of 3-alkylideneoxindoles via palladium-catalyzed domino reactions [J].

Yanada, R ;

Obika, S ;

Inokuma, T ;

Yanada, K ;

Yamashita, M ;

Ohta, S ;

Takemoto, Y .

JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (17) :6972-6975

[33] Stereoselective synthesis of 3-alkylideneoxindoles using tandem in-mediated carbometalation and Pd-catalyzed cross-coupling reaction [J].

Yanada, R ;

Obika, S ;

Oyama, M ;

Takemoto, Y .

ORGANIC LETTERS, 2004, 6 (16) :2825-2828

[34] Enantioselective rhodium-catalyzed [2+2+2]cycloaddition of alkenyl isocyanates and terminal alkynes: Application to the total synthesis of (+)-lasubine II [J].

Yu, Robert T. ;

Rovis, Tomislav .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (38) :12370-12371

[35] Directly observed transmetalation from boron to rhodium.: β-aryl elimination from Rh(I) arylboronates and diarylborinates [J].

Zhao, Pinjing ;

Incarvito, Christopher D. ;

Hartwig, John F. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (07) :1876-+

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