Enantioselective Allenylation of Ketimines Derived from Isatins Using Chiral Bis(imidazoline)-Palladium Catalysts

被引：4

作者：

Oyamada, Yusuke ^{[1
]}

Yamasaki, Shintaro ^{[1
]}

Tsuzuki, Mika ^{[1
]}

Kitagawa, Takumi ^{[1
]}

Kondo, Masaru ^{[1
,2
]}

Sasamori, Takahiro ^{[3
,4
]}

Nakamura, Shuichi ^{[1
]}

机构：

[1] Nagoya Inst Technol, Grad Sch Engn, Dept Life Sci & Appl Chem, Showa Ku, Nagoya, Aichi 4668555, Japan

[2] Ibaraki Univ, Grad Sch Sci & Engn, Dept Mat Sci & Engn, 4-12-1 Naka Narusawa, Hitachi, Ibaraki 3168511, Japan

[3] Univ Tsukuba, Fac Pure & Appl Sci, 1-1-1 Tennodai, Tsukuba, Ibaraki 3058571, Japan

[4] Univ Tsukuba, Tsukuba Res Ctr Energy Mat Sci TREMS, 1-1-1 Tennodai, Tsukuba, Ibaraki 3058571, Japan

来源：

ADVANCED SYNTHESIS & CATALYSIS | 2022年 / 364卷 / 24期

关键词：

ketimines; allenes; chiral allenylamines; bis(imidazoline); palladium; enantioselectivity; VINYLOGOUS MANNICH REACTION; PALLADIUM PINCER COMPLEXES; ALPHA-AMINO-ACIDS; ASYMMETRIC-SYNTHESIS; PROPARGYLATION REACTIONS; KETONES; IMINES; HOMOALLENYLAMIDES; CONSTRUCTION; INHIBITORS;

D O I：

10.1002/adsc.202201017

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

The catalytic enantioselective allenylation of ketimines derived from isatins is described. Products with high regio- and enantioselectivities were obtained in the presence of a bis(imidazoline)-palladium catalyst. The obtained products were then converted into various chiral amines. The stereoselectivity origin was revealed by DFT calculations of the transition state.

引用

页码：4255 / 4259

页数：5

共 50 条

[1] Catalytic Enantioselective Allylation of Ketimines by Using Palladium Pincer Complexes with Chiral Bis(imidazoline)s
Nakamura, Shuichi
Hyodo, Kengo
Nakamura, Masayuki
Nakane, Daisuke
Masuda, Hideki
CHEMISTRY-A EUROPEAN JOURNAL, 2013, 19 (23) : 7304 - 7309
[2] Catalytic Enantioselective Reaction of -Aminoacetonitriles Using Chiral Bis(imidazoline) Palladium Catalysts
Kondo, Masaru
Nishi, Tomoki
Hatanaka, Tsubasa
Funahashi, Yasuhiro
Nakamura, Shuichi
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2015, 54 (28) : 8198 - 8202
[3] Enantioselective Propargylation and Allenylation of Isatins Using Chiral Box-Copper/Zinc Catalysts
Zhao, Ni
Cheng, Shuai-Ru
Ma, Hui-Juan
Zhang, Wei-Wei
Ma, Guo-rong
Wang, Pei
JOURNAL OF ORGANIC CHEMISTRY, 2025, 90 (12): : 4435 - 4439
[4] Catalytic Enantioselective Reaction of -Phenylthioacetonitriles with Imines Using Chiral Bis(imidazoline)-Palladium Catalysts
Kondo, Masaru
Kobayashi, Natsumi
Hatanaka, Tsubasa
Funahashi, Yasuhiro
Nakamura, Shuichi
CHEMISTRY-A EUROPEAN JOURNAL, 2015, 21 (25) : 9066 - 9070
[5] Organocatalytic Enantioselective Peroxidation of Ketimines Derived from Isatins
Nakamura, Shuichi
Takahashi, Shun
ORGANIC LETTERS, 2015, 17 (11) : 2590 - 2593
[6] Enantioselective Vinylogous Mannich Reaction of Acyclic Vinylketene Silyl Acetals with Ketimines Using Chiral Bis(imidazoline)-Cu(II) Catalysts
Nakamura, Shuichi
Matsuzaka, Koichi
Hatanaka, Tsubasa
Funahashi, Yasuhiro
ORGANIC LETTERS, 2020, 22 (08) : 2868 - 2872
[7] Zn-Catalyzed enantioselective allylation and allenylation of isatins by virtue of a proline-derived chiral ligand
Li, Kuiliang
Sun, Xiang
Zhao, Shuangshuang
Li, Tong
Zha, Zhenggen
Wang, Zhiyong
CHEMICAL COMMUNICATIONS, 2022, 58 (13) : 2156 - 2159
[8] Imidazolylpyridine-In(OTf)3 catalyzed enantioselective allylation of ketimines derived from isatins
Chen, Tingting
Cai, Chun
ORGANIC & BIOMOLECULAR CHEMISTRY, 2016, 14 (22) : 5019 - 5022
[9] Enantioselective aza-Friedel-Crafts reaction of cyclic ketimines with indoles using chiral imidazoline-phosphoric acid catalysts
Nakamura, Shuichi
Furukawa, Takashi
Hatanaka, Tsubasa
Funahashi, Yasuhiro
CHEMICAL COMMUNICATIONS, 2018, 54 (31) : 3811 - 3814
[10] Catalytic Enantioselective Reaction of Allenylnitriles with Imines Using Chiral Bis(imidazoline)s Palladium(II) Pincer Complexes
Kondo, Masaru
Omori, Masashi
Hatanaka, Tsubasa
Funahashi, Yasuhiro
Nakamura, Shuichi
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2017, 56 (30) : 8677 - 8680

← 1 2 3 4 5 →