Novel Methodology for the Efficient Synthesis of 3-Aryloxindoles: [1,2]-Phospha-Brook Rearrangement-Palladium-Catalyzed Cross-Coupling Sequence

被引：16

作者：

Kondoh, Azusa ^{[1
]}

Takei, Akira ^{[2
]}

Terada, Masahiro ^{[1
,2
]}

机构：

[1] Tohoku Univ, Grad Sch Sci, Res & Analyt Ctr Giant Mol, Aoba Ku, Sendai, Miyagi 9808578, Japan

[2] Tohoku Univ, Grad Sch Sci, Dept Chem, Aoba Ku, Sendai, Miyagi 9808578, Japan

来源：

SYNLETT | 2016年 / 27卷 / 12期

基金：

日本学术振兴会;

关键词：

oxindole derivatives; phospha-Brook rearrangement; BrOnsted base catalysis; cross-coupling; palladium catalyst; ASYMMETRIC MICHAEL ADDITION; PHOSPHA-BROOK REARRANGEMENT; ACYL ANION EQUIVALENTS; ALPHA-ARYLATION; BRONSTED BASE; INTRAMOLECULAR CYCLIZATION; BENZYLIC PHOSPHATES; INDOLE ALKALOIDS; NATURAL-PRODUCTS; OXINDOLES;

D O I：

10.1055/s-0035-1561859

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A novel methodology for the efficient synthesis of 3-aryloxindoles from isatin derivatives was developed. The methodology involves the formation of an oxindole having a phosphate moiety at the C-3 position via the [1,2]-phospha-Brook rearrangement under BrOnsted base catalysis followed by palladium-catalyzed cross-coupling with aryl boron reagents. The one-pot synthesis of 3-aryloxindoles from isatin derivatives is also described.

引用

页码：1848 / 1853

页数：6

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