Asymmetric synthesis of [7]helicene-like molecules

被引：73

作者：

Stará, IG ^{[1
]}

Alexandrová, Z ^{[1
]}

Teply, F ^{[1
]}

Sehnal, P ^{[1
]}

Stary, I ^{[1
]}

Saman, D ^{[1
]}

Budesínsky, M ^{[1
]}

Cvacka, J ^{[1
]}

机构：

[1] Acad Sci Czech Republ, Inst Organ Chem & Biochem, CR-16610 Prague, Czech Republic

来源：

ORGANIC LETTERS | 2005年 / 7卷 / 13期

关键词：

D O I：

10.1021/ol047311p

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A new approach to nonracemic [7]helicene-like molecules has been developed. Stereoselective Col-mediated [2 + 2 + 2] cycloisomerization of aromatic triynes containing an asymmetric carbon atom produces [7]helicene-like scaffolds in diastereomeric ratios up to 100:0. This central-to-helical chirality transfer can be controlled by the absolute configuration at the asymmetric center and by the presence of carbon substituents.

引用

页码：2547 / 2550

页数：4

共 50 条

[21] Synthesis of methoxy substituted centrally chiral triynes as precursors of functionalised nonracemic helicene-like compounds
Krausova, Zuzana
Sehnal, Petr
Teply, Filip
Stara, Irena G.
Stary, Ivo
Saman, David
Cvacka, Josef
Fidler, Pavel
COLLECTION OF CZECHOSLOVAK CHEMICAL COMMUNICATIONS, 2007, 72 (11) : 1499 - 1522
[22] D-π-A Type [7]Helicene-like Imide Derivatives with Tunable Photophysical Properties and Circularly Polarized Luminescence
Li, Linkuo
Xu, Kunhan
Qi, Ting
CHEMISTRY-A EUROPEAN JOURNAL, 2024, 30 (71)
[23] A [2+2+2] cyclization strategy for the synthesis of phosphorus embedding [6]helicene-like structures
Aillard, Paul
Retailleau, Pascal
Voituriez, Arnaud
Marinetti, Angela
CHEMICAL COMMUNICATIONS, 2014, 50 (17) : 2199 - 2201
[24] Efficient Dibenzo[c]acridine Helicene-like Synthesis and Resolution: Scaleup, Structural Control, and High Chiroptical Properties
Jierry, Loic
Harthong, Steven
Aronica, Christophe
Mulatier, Jean-Christophe
Guy, Laure
Guys, Stephan
ORGANIC LETTERS, 2012, 14 (01) : 288 - 291
[25] Ultrafast excited-state dynamics of thin films consisting of helicene-like molecules based on dibenzo[c,h]acridine
Morgenroth, Marius
Scholz, Mirko
Guy, Laure
Oum, Kawon
Lenzer, Thomas
MOLECULAR PHYSICS, 2021, 119 (17-18)
[26] Chiral amplification in a cyanobiphenyl nematic liquid crystal doped with helicene-like derivatives
Ferrarini, Alberta
Pieraccini, Silvia
Masiero, Stefano
Spada, Gian Piero
BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, 2009, 5
[27] Synthesis and properties of [7] helicene and [7] helicene-like compounds with a cyclopenta[1,2-b: 4,3-b'] dithiophene or dithieno[2,3-b: 3',2'-d] heterole skeleton
Uematsu, K.
Noguchi, K.
Nakano, K.
PHYSICAL CHEMISTRY CHEMICAL PHYSICS, 2018, 20 (05) : 3286 - 3295
[28] STUDIES IN HELICENE SERIES - NMR EVIDENCE OF HELICENE-LIKE CONFORMATIONS IN CIS 1,2-DIARYLETHYLENES .17.
MARTIN, RH
SCHURTER, JJ
RUELLE, JJ
DEFAY, N
FIGEYS, HP
LEVAN, K
HELVETICA CHIMICA ACTA, 1972, 55 (06) : 2241 - &
[29] Synthesis of 2-Phospha[7]helicene, a Helicene with a Terminal
Beranek, Tomas
Jakubec, Martin
Sykora, Jan
Cisarova, Ivana
Zadny, Jaroslav
Storch, Jan
ORGANIC LETTERS, 2022, 24 (26) : 4756 - 4761
[30] Rhodium-Catalyzed Highly Diastereo- and Enantioselective Synthesis of a Configurationally Stable S-Shaped Double Helicene-Like Molecule
Kinoshita, Suzuka
Yamano, Ryota
Shibata, Yu
Tanaka, Yusuke
Hanada, Kyoichi
Matsumoto, Takashi
Miyamoto, Kazunori
Muranaka, Atsuya
Uchiyama, Masanobu
Tanaka, Ken
Advanced Materials, 2020, 132 (27) : 11113 - 11120

← 1 2 3 4 5 →