Manganese-Catalyzed Ring-Opening Coupling Reactions of Cyclopropanols with Enones

被引：40

作者：

Zhang, Yong-Hui ^{[1
,2
,3
]}

Zhang, Wen-Wei ^{[3
]}

Zhang, Ze-Yu ^{[1
]}

Zhao, Kai ^{[1
]}

Loh, Teck-Peng ^{[1
,2
]}

机构：

[1] Nanjing Tech Univ, Jiangsu Natl Synerget Innovat Ctr Adv Mat, Sch Chem & Mol Engn, Inst Adv Synth, Nanjing 211816, Jiangsu, Peoples R China

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

[3] BGI Shenzhen, Shenzhen 518083, Peoples R China

来源：

ORGANIC LETTERS | 2019年 / 21卷 / 13期

基金：

中国国家自然科学基金;

关键词：

C-H ACTIVATION; BETA-CARBONYL RADICALS; BOND-CLEAVAGE; REGIOSPECIFIC SYNTHESIS; 7-MEMBERED CARBOCYCLES; OXIDATIVE CLEAVAGE; STRATEGY; DERIVATIVES; KETONES; ALKYL;

D O I：

10.1021/acs.orglett.9b01703

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A manganese-catalyzed ring-opening coupling reaction of cyclopropanols with enones for the facile and efficient preparation of 1,6-diketones is described. A wide array of synthetically important 1,6-diketones bearing manifold functional groups are obtained with up to 93% yield. These reactions feature broad substrate scopes, environmentally benign conditions, inexpensive catalyst, and operational simplicity.

引用

页码：5101 / 5105

页数：5

共 50 条

[1] Manganese-catalyzed ring-opening carbonylation of cyclobutanol derivatives
Meyer, Tim
Yin, Zhiping
Wu, Xiao-Feng
TETRAHEDRON LETTERS, 2019, 60 (12) : 864 - 867
[2] Manganese-catalyzed ring-opening chlorination of cyclobutanols: regiospecific synthesis of γ-chloroketones
Huan, Leitao
Zhu, Chen
ORGANIC CHEMISTRY FRONTIERS, 2016, 3 (11): : 1467 - 1471
[3] Manganese-Catalyzed Ring-Opening C-C Bond Fluorination of Cyclobutanols
Wang Limei
Liu Xiaoyuan
Zan Jincheng
Sun Shutao
Liu Lei
Li Wei
Liu Xigong
CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2024, 44 (07) : 2333 - 2340
[4] Ring-opening Fluorination of Cyclobutanols and Cyclopropanols Catalyzed by Silver
Ishida, Naoki
Okumura, Shintaro
Nakanishi, Yuuta
Murakami, Masahiro
CHEMISTRY LETTERS, 2015, 44 (06) : 821 - 823
[5] Copper(I)-catalyzed ring-opening cyanation of cyclopropanols
Feng, Yi-Si
Shu, Yong-Jin
Cao, Ping
Xu, Tao
Xu, Hua-Jian
ORGANIC & BIOMOLECULAR CHEMISTRY, 2017, 15 (17) : 3590 - 3593
[6] Nickel-Catalyzed Ring-Opening Allylation of Cyclopropanols via Homoenolate
Sekiguchi, Yoshiya
Lee, Yan Ying
Yoshikai, Naohiko
ORGANIC LETTERS, 2021, 23 (15) : 5993 - 5997
[7] CYCLOPROPANOLS .11. ACID-CATALYZED RING-OPENING OF ARYLCYCLOPROPANOLS
DEPUY, CH
KLEIN, RA
CLARK, JP
JOURNAL OF ORGANIC CHEMISTRY, 1974, 39 (04): : 483 - 486
[8] CYCLOPROPANOLS - SYNTHESIS AND ELECTROPHILIC RING-OPENING
DEPUY, CH
TRANSACTIONS OF THE NEW YORK ACADEMY OF SCIENCES, 1966, 28 (05): : 561 - &
[9] Synthesis of α-methyl ketones by an iridium-catalyzed ring-opening of cyclopropanols
Funk, Timothy W.
Ziegler, Daniel T.
Steffens, Andrew M.
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2011, 241
[10] Ring-Opening Cross-Coupling/Cyclization Reaction of Cyclopropanols with Organic Compounds
Doraghi, Fatemeh
Aledavoud, Seyedeh Pegah
Fakhrioliaei, Azadeh
Larijani, Bagher
Mahdavi, Mohammad
CHEMISTRYSELECT, 2023, 8 (32):

← 1 2 3 4 5 →