Synthesis of densely functionalised arenes using [2+2+2] cycloaddition reactions

被引:20
作者
Clayden, Jonathan [1 ]
Moran, Wesley J. [1 ]
机构
[1] Univ Manchester, Sch Chem, Manchester M13 9PL, Lancs, England
基金
英国工程与自然科学研究理事会;
关键词
D O I
10.1039/b700353f
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Rh(I)-catalysed [2 + 2 + 2] cycloaddition allows the synthesis of aryl ethers and diaryl methanes containing a high degree of steric hindrance from relatively simple diyne and alkyne precursors. The diarylmethanes made in this way show no evidence in their NMR spectra, however, of rotational restriction.
引用
收藏
页码:1028 / 1030
页数:3
相关论文
共 26 条
[1]   Slow interconversion of enantiomeric conformers or atropisomers of anilide and urea derivatives of 2-substituted anilines [J].
Adler, T ;
Bonjoch, J ;
Clayden, J ;
Font-Bardía, M ;
Pickworth, M ;
Solans, X ;
Solé, D ;
Vallverdú, L .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2005, 3 (17) :3173-3183
[2]   The behavior of 1,n-enynes in the presence of transition metals [J].
Aubert, C ;
Buisine, O ;
Malacria, M .
CHEMICAL REVIEWS, 2002, 102 (03) :813-834
[3]   Three groups good, four groups bad?: Atropisomerism in ortho-substituted diaryl ethers [J].
Betson, Mark S. ;
Clayden, Jonathan ;
Worrall, Christopher R. ;
Peace, Simon .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (35) :5803-5807
[4]   Synthesis of multiply ortho-substituted diaryl ethers via lithiation and oxidation of a dibenzosiloxane (phenoxasilin) [J].
Betson, MS ;
Clayden, J .
SYNLETT, 2006, (05) :745-746
[5]   Atroposelective synthesis of axially chiral biaryl compounds [J].
Bringmann, G ;
Mortimer, AJP ;
Keller, PA ;
Gresser, MJ ;
Garner, J ;
Breuning, M .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (34) :5384-5427
[6]   Atropisomers and near-atropisomers: achieving stereoselectivity by exploiting the conformational preferences of aromatic amides [J].
Clayden, J .
CHEMICAL COMMUNICATIONS, 2004, (02) :127-135
[7]   Preliminary in vitro studies on two potent, water-soluble trimethoprim analogues with exceptional species selectivity against dihydrofolate reductase from Pneumocystis carinii and Mycobacterium avium [J].
Forsch, RA ;
Queener, SF ;
Rosowsky, A .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2004, 14 (07) :1811-1815
[8]   Metal-assisted cycloaddition reactions in organotransition metal chemistry [J].
Fruhauf, HW .
CHEMICAL REVIEWS, 1997, 97 (03) :523-596
[9]   Conformationally restricted analogues of trimethoprim: 2,6-diamino-8-substituted purines as potential dihydrofolate reductase inhibitors from Pneumocystis carinii and Toxoplasma gondii [J].
Gangjee, A ;
Vasudevan, A ;
Queener, SF .
JOURNAL OF MEDICINAL CHEMISTRY, 1997, 40 (19) :3032-3039
[10]   Synthesis and dihydrofolate reductase inhibitory activities of 2,4-diamino-5-deaza and 2,4-diamino-5,10-dideaza lipophilic antifolates [J].
Gangjee, A ;
Devraj, R ;
Queener, SF .
JOURNAL OF MEDICINAL CHEMISTRY, 1997, 40 (04) :470-478