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
收藏
页码：1848 / 1853
页数：6
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