Enantioselective Synthesis of P-Chiral Phosphine Oxides Bearing an All-Carbon Quaternary Stereogenic Center via Palladium-Catalyzed Domino Heck-Suzuki Reaction

被引：3

作者：

Zhao, Siyu ^{[1
]}

Liu, Jiahao ^{[1
]}

Xu, Xunfang ^{[1
]}

Chen, Xuemei ^{[1
]}

Kato, Terumasa ^{[1
,2
,3
]}

Wang, Zhe ^{[1
,2
]}

Liu, Yan ^{[1
,2
]}

Maruoka, Keiji ^{[1
,2
,3
]}

机构：

[1] Guangdong Univ Technol, Sch Chem Engn & Light Ind, Guangzhou 510006, Peoples R China

[2] Guangdong Univ Technol, Guangdong Prov Key Lab Plant Resources Biorefinery, Guangzhou 510006, Peoples R China

[3] Kyoto Univ, Grad Sch Pharmaceut Sci, Lab Organocatalyt Chem, Kyoto 6068501, Japan

来源：

ACS CATALYSIS | 2024年 / 14卷 / 19期

基金：

中国国家自然科学基金;

关键词：

palladium catalysis; domino Heck; P-stereogenic centers; desymmetrization; all-carbonquaternary stereocenters; ASYMMETRIC-SYNTHESIS; ARYLATION; DESYMMETRIZATION; STEREOCENTERS; CONSTRUCTION; PHOSPHORUS;

D O I：

10.1021/acscatal.4c04958

中图分类号：

O64 [物理化学（理论化学）、化学物理学];

学科分类号：

070304 ; 081704 ;

摘要：

An approach has been developed for the enantioselective synthesis of P-chiral phosphine oxides bearing an all-carbon quaternary stereogenic center via a Pd-catalyzed domino Heck-Suzuki reaction. The origin of the mechanistic preference leading to high diastereo- and enantioselectivities under the Pd catalysis based on a TADDOL-derived phosphoramidite ligand was rationalized on the basis of DFT calculations.

引用

页码：14762 / 14768

页数：7

共 26 条

[21] Enantioselective Synthesis of Oxetanes Bearing All-Carbon Quaternary Stereocenters via Iridium-Catalyzed C-C Bond-Forming Transfer Hydrogenation
Guo, Yi-An
Lee, Wonchul
Krische, Michael J.
CHEMISTRY-A EUROPEAN JOURNAL, 2017, 23 (11) : 2557 - 2559
[22] Cu-Catalyzed Diastereo- and Enantioselective Synthesis of Homopropargyl Amines Bearing All-Carbon Quaternary Stereocenters via Chirality Transfer of Hindered Allenylcopper Species
He, Jing
Yoon, Wan Seok
Yun, Jaesook
ACS CATALYSIS, 2024, 15 (01): : 578 - 584
[23] Synthesis of Chiral Bis(3-indolyl)methanes Bearing a Trifluoromethylated All-Carbon Quaternary Stereocenter via Nickel-Catalyzed Asymmetric Friedel-Crafts Alkylation Reaction
Zhu, Wen-Jing
Gong, Jun-Fang
Song, Mao-Ping
JOURNAL OF ORGANIC CHEMISTRY, 2020, 85 (15): : 9525 - 9537
[24] Enantioselective Synthesis of an All-Carbon Quaternary Stereocenter by Chiral Br?nsted Acid-Catalyzed Friedel-Crafts-Type Reaction between Pyrroles and 3-Indolylmethanols
Uchikura, Tatsuhiro
Sanchez-Sordo, Irene
Yoshimura, Tatsuhiko
Makino, Yudai
Osakabe, Hiroto
Akiyama, Takahiko
JOURNAL OF ORGANIC CHEMISTRY, 2023, 88 (12): : 7774 - 7783
[25] Enantioselective synthesis of tetrahydrocyclopenta[b]indole bearing a chiral quaternary carbon center via Pd(II)-SPRIX-catalyzed C-H activation
Abozeid, Mohamed Ahmed
Sairenji, Shiho
Takizawa, Shinobu
Fujita, Makoto
Sasai, Hiroaki
CHEMICAL COMMUNICATIONS, 2017, 53 (51) : 6887 - 6890
[26] Construction of Benzofuran-3(2H)-one Scaffolds Bearing a C2 Quaternary Center via Palladium-Catalyzed Carbonylative Heck Reaction using Mo(CO)6 as Carbonyl Source
Guo, Wenting
Gong, Houhong
Jiao, Xiaojing
Liao, Yueling
Pei, Xiaoqin
Xia, Ming
Zhou, Hualan
Wang, Huiyan
Hu, Weiming
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2024, 27 (38)

← 1 2 3 →