Iron-catalysed enantioselective carbometalation of azabicycloalkenes

被引：5

作者：

Adak, Laksmikanta ^{[1
,2
,3
]}

Jin, Masayoshi ^{[1
,2
,4
]}

Saito, Shota ^{[1
,2
]}

Kawabata, Tatsuya ^{[1
,2
]}

Itoh, Takuma ^{[1
,2
]}

Ito, Shingo ^{[1
,2
,5
]}

Sharma, Akhilesh K. ^{[1
,2
]}

Gower, Nicholas J. ^{[1
,2
]}

Cogswell, Paul ^{[1
,2
]}

Geldsetzer, Jan ^{[1
,2
]}

Takaya, Hikaru ^{[1
,2
]}

Isozaki, Katsuhiro ^{[1
,2
]}

Nakamura, Masaharu ^{[1
,2
]}

机构：

[1] Kyoto Univ, Int Res Ctr Elements Sci, Inst Chem Res ICR, Kyoto 6110011, Japan

[2] Kyoto Univ, Dept Energy & Hydrocarbon Chem, Grad Sch Engn, Nishikyo ku, Kyoto 6158510, Japan

[3] Indian Inst Engn Sci & Technol, Dept Chem, Bot Garden, Howrah 711103, India

[4] Daiichi Sankyo Co Ltd, Proc Technol Res Labs, Pharmaceut Technol Div, 1-12-1 Shinomiya, Hiratsuka, Kanagawa 2540014, Japan

[5] Nanyang Technol Univ, Sch Phys & Math Sci, Div Chem & Biol Chem, 21 Nanyang Link, Singapore 637371, Singapore

来源：

CHEMICAL COMMUNICATIONS | 2021年 / 57卷 / 57期

基金：

日本科学技术振兴机构;

关键词：

RING-OPENING REACTIONS; CROSS-COUPLING REACTIONS; OXABICYCLIC ALKENES; AZABICYCLIC ALKENES; RHODIUM; COMPLEXES; EPIBATIDINE; LIGAND; METAL; DESYMMETRIZATION;

D O I：

10.1039/d1cc02387j

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The first enantioselective carbometalation reaction of azabicycloalkenes has been achieved by iron catalysis to in situ form optically active organozinc intermediates, which are amenable to further synthetic elaborations. The observed chiral induction, along with the DFT and XAS analyses, reveals the direct coordination of the chiral phosphine ligand to the iron centre during the carbon-carbon and carbon-metal bond forming step. This new class of iron-catalysed asymmetric reaction will contribute to the synthesis and production of bioactive molecules.

引用

页码：6975 / 6978

页数：5

共 62 条

[1] Synthesis of Aryl C-Glycosides via Iron-Catalyzed Cross Coupling of Halosugars: Stereoselective Anomeric Arylation of Glycosyl Radicals [J].