Ruthenium-Catalyzed Enantioselective Propargylic Phosphinylation of Propargylic Alcohols with Phosphine Oxides

被引：39

作者：

Liu, Shiyao ^{[1
]}

Tanabe, Yoshiaki ^{[1
]}

Kuriyama, Shogo ^{[1
]}

Sakata, Ken ^{[2
]}

Nishibayashi, Yoshiaki ^{[1
]}

机构：

[1] Univ Tokyo, Sch Engn, Dept Appl Chem, Bunkyo Ku, Tokyo 1138656, Japan

[2] Toho Univ, Fac Pharmaceut Sci, Funabashi, Chiba 2748510, Japan

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2021年 / 60卷 / 20期

关键词：

DFT calculations; enantioselective reactions; propargylic phosphinylation; propargylic substitution reaction; ruthenium; ASYMMETRIC ADDITION; SUBSTITUTION-REACTIONS; PHOSPHORUS LIGANDS; SYNTHETIC APPROACH; 3+2 CYCLOADDITION; ACID; ESTERS; DIARYLPHOSPHINES; HYDROPHOSPHONYLATION; ETHERIFICATION;

D O I：

10.1002/anie.202102779

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The development of transition metal-catalyzed enantioselective propargylic substitution reactions has gained much progress in recent years, however, no successful example with phosphorus-centered nucleophiles has yet been reported until now. Herein, we report the first successful example of ruthenium-catalyzed enantioselective propargylic substitution reactions of propargylic alcohols with diarylphosphine oxides as phosphorus-centered nucleophiles. This synthetic approach provides a new method to prepare chiral phosphorus-containing organic compounds.

引用

页码：11231 / 11236

页数：6

共 98 条

[51] Ni-Catalyzed Asymmetric Allylation of Secondary Phosphine Oxides [J].

Liu, Xu-Teng ;

Zhang, Ya-Qjan ;

Han, Xue-Yu ;

Sun, Shi-Ping ;

Zhang, Qing-Wei .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2019, 141 (42) :16584-16589

[52] Asymmetric Propargylic Radical Cyanation Enabled by Dual Organophotoredox and Copper Catalysis [J].

Lu, Fu-Dong ;

Liu, Dan ;

Zhu, Lei ;

Lu, Liang-Qiu ;

Yang, Qian ;

Zhou, Quan-Quan ;

Wei, Yi ;

Lan, Yu ;

Xiao, Wen-Jing .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2019, 141 (15) :6167-6172

[53] Palladium-Catalyzed Asymmetric Addition of Diarylphosphines to α,β-Unsaturated Sulfonic Esters for the Synthesis of Chiral Phosphine Sulfonate Compounds [J].

Lu, Junzhu ;

Ye, Jinxing ;

Duan, Wei-Liang .

ORGANIC LETTERS, 2013, 15 (19) :5016-5019

[54] Redox deracemization of diarylmethyl alkynes [J].

Ma, Yingang ;

Liu, Xigong ;

Mao, Ying ;

Huang, Jiancheng ;

Ma, Shutao ;

Liu, Lei .

ORGANIC CHEMISTRY FRONTIERS, 2020, 7 (17) :2526-2530

[55] Chiral phosphoric acid catalysis: from numbers to insights [J].

Maji, Rajat ;

Mallojjala, Sharath Chandra ;

Wheeler, Steven E. .

CHEMICAL SOCIETY REVIEWS, 2018, 47 (04) :1142-1158

[56] Ruthenium-catalyzed enantioselective prolpargylation of aromatic compounds with propargylic alcohols via allenylidene intermediates [J].

Matsuzawa, Hiroshi ;

Miyake, Yoshihiro ;

Nishibayashi, Yoshiaki .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (34) :6488-6491

[57] Double phosphinylation of propargylic alcohols: A novel synthetic route to 1,2-bis(diphenylphosphino)ethane derivatives [J].

Milton, MD ;

Onodera, G ;

Nishibayashi, Y ;

Uemura, S .

ORGANIC LETTERS, 2004, 6 (22) :3993-3995

[58]

Miyake Y., 2013, ANGEW CHEM, V125, P1802

[59] Ruthenium-Triggered Ring Opening of Ethynylcyclopropanes: [3+2] Cycloaddition with Aldehydes and Aldimines Involving Metal Allenylidene Intermediates [J].

Miyake, Yoshihiro ;

Endo, Satoshi ;

Moriyama, Taichi ;

Sakata, Ken ;

Nishibayashi, Yoshiaki .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (06) :1758-1762

[60] Copper-Catalyzed Enantioselective Propargylic Etherification of Propargylic Esters with Alcohols [J].

Nakajima, Kazunari ;

Shibata, Masashi ;

Nishibayashi, Yoshiaki .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2015, 137 (07) :2472-2475

← 1 2 3 4 5 6 7 8 9 10 →