Exploring F/CF3 substituted oxocarbenium ions for the diastereoselective assembly of highly substituted tetrahydrofurans

被引：0

作者：

Fernandes, Anthony J. ^{[1
]}

Michelet, Bastien ^{[2
]}

Panossian, Armen ^{[1
]}

Martin-Mingot, Agnes ^{[2
]}

Leroux, Frederic R. ^{[1
]}

Thibaudeau, Sebastien ^{[2
]}

机构：

[1] Univ Strasbourg, Univ Haute Alsace, CNRS, UMR 7042 LIMA,ECPM, 25 Rue Becquerel, F-67087 Strasbourg, Alsace, France

[2] Univ Poitiers, Equipe Synth Organ, CNRS, UMR 7285,IC2MP, 4 Rue Michel Brunet, F-86073 Poitiers 9, France

来源：

CHEMICAL COMMUNICATIONS | 2023年 / 59卷 / 27期

关键词：

NUCLEOPHILES; REDUCTION; LIGNANS; EXPLAIN;

D O I：

10.1039/d2cc06521e

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Understanding the influence of emerging fluorinated motifs is of a crucial importance in the context of the exponentially growing exploitation of fluorine in many fields. Herein, we report on the dramatic effect of a local partial charge inversion by replacing a CHCH3 group by a CFCF3. This strategy allows the diastereoselective reduction of 5-membered ring oxocarbenium ions to access highly substituted tetrahydrofurans.

引用

页码：4083 / 4086

页数：4

共 50 条

[41] Diastereoselective Synthesis of Highly Substituted Tetrahydrofurans by Pd-Catalyzed Tandem Oxidative Cyclization Redox Relay Reactions Controlled by Intramolecular Hydrogen Bonding
Brooks, Joshua L.
Xu, Liping
Wiest, Olaf
Tan, Derek S.
JOURNAL OF ORGANIC CHEMISTRY, 2017, 82 (01): : 57 - 75
[42] F and CF3 substituted solution processable oligo para-phenylenevinylene for ambipolar and hole-transporting organic field effect transistors
Chini, Mrinmoy Kumar
Das, Chayanika
Chatterjee, Shyambo
CHEMICAL PHYSICS LETTERS, 2016, 657 : 26 - 32
[43] One- and two-photon solvatochromism of the fluorescent dye Nile Red and its CF3, F and Br-substituted analogues
Hornum, Mick
Reinholdt, Peter
Zareba, Jan K.
Jensen, Brian B.
Wustner, Daniel
Samoc, Marek
Nielsen, Poul
Kongsted, Jacob
PHOTOCHEMICAL & PHOTOBIOLOGICAL SCIENCES, 2020, 19 (10) : 1382 - 1391
[44] Palladium-Catalyzed Negishi Coupling of α-CF3 Oxiranyl Zincate: Access to Chiral CF3-Substituted Benzylic Tertiary Alcohols
Zhang, Hu
Buchwald, Stephen L.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2017, 139 (33) : 11590 - 11594
[45] One- and two-photon solvatochromism of the fluorescent dye Nile Red and its CF3, F and Br-substituted analogues
Mick Hornum
Peter Reinholdt
Jan K. Zarę ba
Brian B. Jensen
Daniel Wüstner
Marek Samoć
Poul Nielsen
Jacob Kongsted
Photochemical & Photobiological Sciences, 2020, 19 : 1382 - 1391
[46] Formation of synthetically relevant CF3-substituted phenonium ions in superacid media
Fernandes, Anthony J.
Michelet, Bastien
Panossian, Armen
Martin-Mingot, Agnes
Leroux, Frederic R.
Thibaudeau, Sebastien
RSC ADVANCES, 2021, 11 (41) : 25695 - 25699
[47] PREPARATION AND PROPERTIES OF TRIFLUOROMETHYL SUBSTITUTED STANNANES, (CF3)NSNH4-N (N=1-3)
EUJEN, R
JAHN, N
THURMANN, U
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1992, 434 (02) : 159 - 168
[48] Synthesis of CF3, CF2H-Substituted, Epoxide-Fused Heterocycles with Prop-2-ynylsulfonium salts
Wu, Shitong
Cheng, Xi
Yao, Changguang
Yang, Weiran
Zheng, Jing
ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2023, 12 (04)
[49] Highly diastereoselective samarium diiodide induced cyclizations of new 3-substituted indole derivatives
Beemelmanns, Christine
Reissig, Hans-Ulrich
ORGANIC & BIOMOLECULAR CHEMISTRY, 2009, 7 (21) : 4475 - 4480
[50] NITROSYL IRON(II) COMPLEXES OF PORPHYRINS SUBSTITUTED WITH HIGHLY ELECTRON-WITHDRAWING CF3 GROUPS - ELECTRONIC ABSORPTION, MCD AND EPR SPECTRAL STUDY
YOSHIMURA, T
KAMADA, H
TOI, H
INABA, S
OGOSHI, H
INORGANICA CHIMICA ACTA, 1993, 208 (01) : 9 - 15

← 1 2 3 4 5 →