Ir-Catalyzed cyclization of α,ω-dienes with an N-methyl group via two C-H activation steps

被引：5

作者：

Tanaka, Katsumasa ^{[1
]}

Hattori, Hiroshi ^{[1
]}

Yabe, Ryota ^{[1
]}

Nishimura, Takahiro ^{[1
]}

机构：

[1] Osaka City Univ, Grad Sch Sci, Dept Chem, Sumiyoshi, Osaka 5588585, Japan

来源：

CHEMICAL COMMUNICATIONS | 2022年 / 58卷 / 35期

关键词：

BOND ACTIVATION; CYCLOISOMERIZATION; ALKYLATION; DIENES; 1,6-ENYNES; ALKENE;

D O I：

10.1039/d2cc01275h

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Iridium-catalyzed sp(3) C-H alkylation of an N-methyl group with 1,5- and 1,6-dienes proceeded to give five- and six-membered carbocyclic compounds, respectively, in high yields. The reaction involves intermolecular alkylation of the N-methyl group with a vinyl moiety and subsequent intramolecular cyclization at the beta-position of the initially formed alkylated intermediate. The reaction using a chiral bidentate phosphine ligand enabled the asymmetric synthesis of the cyclic compounds.

引用

页码：5371 / 5374

页数：4

共 48 条

[1] Stereoselectivity of Metal-Catalyzed Cyclizations of 1,6-Dienes [J].

Aissa, Christophe .

SYNLETT, 2014, 25 (17) :2379-2384

[2] Diastereoselective Cyclization of 1,5-Dienes with the C-H Bond of Pyridine Catalyzed by a Cationic Mono(phosphinoamide) Alkyl Scandium Complex [J].

Chen, Yanhui ;

Song, Di ;

Li, Jing ;

Hu, Xiaoyan ;

Bi, Xianjia ;

Jiang, Tao ;

Hou, Zhaomin .

CHEMCATCHEM, 2018, 10 (01) :159-164

[3] Enantioselective Rhodium-Catalyzed Cycloisomerization of 1,6-Allenynes to access 5/6-Fused Bicycle[4.3.0] nonadienes [J].

Deng, Xu ;

Shi, Li-Yang ;

Lan, Jialing ;

Guan, Yu-Qing ;

Zhang, Xiaoyong ;

Lv, Hui ;

Chung, Lung Wa ;

Zhang, Xumu .

NATURE COMMUNICATIONS, 2019, 10 (1)

[4] Iridium(I)-Catalyzed Intramolecular Cycloisomerization of Enynes: Scope and Mechanistic Course [J].

Fernandez, David F. ;

Rodrigues, Catarina A. B. ;

Calvelo, Martin ;

Gulias, Moises ;

Mascarenas, Jose L. ;

Lopez, Fernando .

ACS CATALYSIS, 2018, 8 (08) :7397-7402

[5] Transition-Metal-Catalyzed Annulations Involving the Activation of C(sp3)-H Bonds [J].

Font, Marc ;

Gulias, Moises ;

Mascarenas, Jose Luis .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2022, 61 (06)

[6] REGIOSELECTION AND ENANTIOSELECTION IN ORGANOLANTHANIDE-CATALYZED OLEFIN HYDROSILYLATION - A KINETIC AND MECHANISTIC STUDY [J].

FU, PF ;

BRARD, L ;

LI, YW ;

MARKS, TJ .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1995, 117 (27) :7157-7168

[7] Iridium-Catalyzed Sequential sp3 C-H Alkylation of an N-Methyl Group with Alkenes Towards the Synthesis of α-Substituted Amines [J].

Hattori, Hiroshi ;

Nishimura, Takahiro .

ADVANCED SYNTHESIS & CATALYSIS, 2018, 360 (24) :4827-4831

[8] Copper-Catalyzed Asymmetric Borylative Cyclization of Cyclohexadienone-Containing 1,6-Dienes [J].

He, Cheng-Yu ;

Li, Qing-Hua ;

Wang, Xin ;

Wang, Feng ;

Tian, Ping ;

Lin, Guo-Qiang .

ADVANCED SYNTHESIS & CATALYSIS, 2020, 362 (04) :765-770

[9] Cationic Co(I) Catalysts for Regiodivergent Hydroalkenylation of 1,6-Enynes: An Uncommon cis-β-C-H Activation Leads to Z-Selective Coupling of Acrylates [J].

Herbort, James H. ;

Lalisse, Remy F. ;

Hadad, Christopher M. ;

RajanBabu, T., V .

ACS CATALYSIS, 2021, 11 (15) :9605-9617

[10] Alkene and diene hydrosilylations catalyzed by lanthanum tris[bis(trimethylsilyl)amide [J].

Horino, Y ;

Livinghouse, T .

ORGANOMETALLICS, 2004, 23 (01) :12-14

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