Dinuclear Zinc-Catalyzed Asymmetric Desymmetrization of Cyclopentendiones: Access to Functional Cyclopentanediones Bearing an All-carbon Quaternary Stereocenter

被引：1

作者：

Du, Si-Si ^{[1
]}

Zhai, Ying-Hui ^{[1
]}

Zhang, Cui ^{[1
]}

Wang, Min-Can ^{[1
]}

Jia, Shi-Kun ^{[1
]}

Mei, Guang-Jian ^{[1
]}

Hua, Yuan-Zhao ^{[1
]}

机构：

[1] Zhengzhou Univ, Inst Green Catalysis, Coll Chem, 100 Sci Rd, Zhengzhou City 450000, Henan Province, Peoples R China

来源：

CHEMISTRY-AN ASIAN JOURNAL | 2023年 / 18卷 / 18期

关键词：

cyclopentendiones; desymmetrization; dinuclear zinc catalyst; MANNICH-TYPE REACTION; ENANTIOSELECTIVE DESYMMETRIZATION; MESO-EPOXIDES; CONSTRUCTION; CYCLOPENTENEDIONES; DESYMMETRISATION; HYDROXYKETONES; ARYLATION; ADDITIONS; AMINES;

D O I：

10.1002/asia.202300591

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The success in the identification of the two enantioisomeric surfaces of electrophiles by dinuclear zinc catalysts is disclosed. This protocol realizes a dinuclear zinc-cocatalyzed desymmetrization of cyclopentendiones using & alpha;-hydroxy aryl ketones as nucleophiles through Michael addition reaction. Under mild conditions, a series of functional cyclopentanediones bearing multiple stereogenic centers including an all-carbon quaternary stereocenter, were obtained in moderate to good yields with excellent stereoselectivities.

引用

页数：5

共 50 条

[41] Asymmetric Three-Component Reaction to Assemble the Acyclic All-Carbon Quaternary Stereocenter via Visible Light and Phosphoric Acid Catalysis
Qiu, Zong-Wang
Long, Liang
Zhu, Zhi-Qiang
Liu, Hong-Fu
Pan, Han-Peng
Ma, Ai-Jun
Peng, Jin-Bao
Wang, Yong-Heng
Gao, Hao
Zhang, Xiang-Zhi
ACS CATALYSIS, 2022, 12 (21): : 13282 - 13291
[42] Asymmetric Synthesis of a Bicyclo[4.3.0]nonene Derivative Bearing a Quaternary Carbon Stereocenter: Desymmetrization of σ-Symmetrical Diketones through Intramolecular Addition of an Alkenyl Anion
Yoshimura, Tomoyuki
Enami, Yuki
Matsuo, Jun-ichi
SYNTHESIS-STUTTGART, 2020, 52 (23): : 3667 - 3674
[43] Asymmetric Synthesis of All-Carbon Quaternary Stereocenters via Desymmetrization of 2,2-Disubstituted 1,3-Propanediols
Lee, Ji Young
You, Young Suk
Kang, Sung Ho
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (06) : 1772 - 1774
[44] Remote Stereocontrol of All-Carbon Quaternary Centers via Cobalt-Catalyzed Asymmetric Olefin Isomerization
Rong, Xianle
Yang, Jie
Liu, Shihan
Lan, Yu
Liu, Qiang
CCS CHEMISTRY, 2023, 5 (06): : 1293 - 1300
[45] Asymmetric α-Photoalkylation of β-Ketocarbonyls by Primary Amine Catalysis: Facile Access to Acyclic All-Carbon Quaternary Stereocenters
Zhu, Yunbo
Zhang, Long
Luo, Sanzhong
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2014, 136 (42) : 14642 - 14645
[46] Asymmetric α-Photoalkylation of β-Ketocarbonyls by Primary Amine Catalysis: Facile Access to Acyclic All-Carbon Quaternary Stereocenters
Zhu, Yunbo
Zhang, Long
Luo, Sanzhong
SYNTHESIS-STUTTGART, 2015, 47 (05): : A34 - A37
[47] Phosphoric Acid Catalyzed Desymmetrization of Bicyclic Bislactones Bearing an All-Carbon Stereogenic Center: Total Syntheses of (-)-Rhazinilam and (-)-Leucomidine B
Gualtierotti, Jean-Baptiste
Pasche, Delphine
Wang, Qian
Zhu, Jieping
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2014, 53 (37) : 9926 - 9930
[48] Enantio- and Diastereoselective Synthesis of Chiral Tetrasubstituted α-Amino Allenoates Bearing a Vicinal All-Carbon Quaternary Stereocenter with Dual-Copper-Catalysis
Sheng, Cheng
Ling, Zheng
Xiao, Junzhe
Yang, Kai
Fang, Xie
Ma, Shengming
Zhang, Wanbin
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2023, 62 (31)
[49] NHC-catalyzed enantioselective synthesis of dihydropyran-4-carbonitriles bearing all-carbon quaternary centers
Wu, Qiuju
Li, Chengcheng
Wang, Weihong
Wang, Hongling
Pan, Dingwu
Zheng, Pengcheng
ORGANIC CHEMISTRY FRONTIERS, 2017, 4 (12): : 2323 - 2326
[50] Iridium-Catalyzed Asymmetric Allylic Alkylation of Boron Enolates to Construct Acyclic All-Carbon Quaternary Stereocenters
Yang, Liu
Yang, Mengzhi
Wang, Zhenchao
Zhao, Wanxiang
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2025,

← 1 2 3 4 5 →