An Imidazoline- Aminophenol ( IAP) Nickel Catalyst: Structure and Catalytic Activity in the Enantioselective 1,4-Addition of 3'- Indolyl-3-Oxindoles to Nitroethylene

被引：22

作者：

Awata, Atsuko ^{[1
]}

Wasai, Makiko ^{[1
]}

Masu, Hyuma ^{[2
]}

Kado, Sayaka ^{[2
]}

Arai, Takayoshi ^{[1
]}

机构：

[1] Chiba Univ, Grad Sch Sci, Dept Chem, Inage Ku, Chiba 2638522, Japan

[2] Chiba Univ, Ctr Analyt Instrumentat, Inage Ku, Chiba 2638522, Japan

来源：

CHEMISTRY-A EUROPEAN JOURNAL | 2014年 / 20卷 / 09期

关键词：

asymmetric catalysis; indole; 1; 4-addition; nickel; tridentate ligands; ASYMMETRIC MICHAEL ADDITION; CONCISE TOTAL-SYNTHESIS; SELECTIVE 3+2 CYCLOADDITION; 3-SUBSTITUTED OXINDOLES; TRYPTOPHAN DERIVATIVES; CONJUGATE ADDITION; CONSTRUCTION; NITROALKENES; COMPLEX; SPIROCYCLOPENTANEOXINDOLES;

D O I：

10.1002/chem.201304456

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The structure of a nickel complex of imidazoline-aminophenol (IAP) prepared from IAP with Ni(OAc)(2) was elucidated as cis-bis(imidazolineaminophenoxide) [Ni(IAP)(2)]. The [Ni(IAP)(2)] complex smoothly promoted catalytic asymmetric 1,4-addition of 3-indolyl-3-oxindole to nitroethylene to provide chiral mixed 3,3-bisindoles with high enantioselectivities. Mechanistic studies using ESI-MS analyses suggest that one IAP ligand dissociated from [Ni(IAP)(2)] to generate the Ni-enolate of 3-indolyl-3-oxindole. From the optically active 3,3-mixed indole adduct, biologically important 3-indolyl-3-pyrrolidinoindoline was successfully synthesized in a three-step reaction sequence.

引用

页码：2470 / 2477

页数：8

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