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1.
A rapid and regioselective preparation of homopropargyl alcohols was reported. In the presence of SnCl2C6HsMe3NBr and microwave irradiation, the mixture of tin-indium and propargyl bromide reacted quickly with aldehydes in aqueous media to produce the homopropargyl alcohols exclusively in high yields. For benzaldehydes bearing different substituents, electronic effect of the substituents affected the reaction, the electron-withdrawing groups promoting the reaction and the electron-donating groups impeding the reaction. The reactions of benzaldehydes bearing an ortho substituent group on the phenyl ring with propargyl bromide may yield a mixture of regioisomers (homopropargyl and homoallenyl alcohols) or a single homoallenic alcohol due to the steric effect. 相似文献
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ZHOU Jing-Yao SUN Guang-Fu ZHANG Ming-Fu JIA Yu WU Shi-HuiDepartment of Chemistry Fudan University Shanghai China 《中国化学》1997,15(4):361-365
This paper reports that the reaction of the propargyl bromides with aldehydes promoted by powdered lead in aqueous media.The selectivity and possible mechanism of these reactions are discussed.The yields of products for reaction of propargyl bromide are 31~71%.The ratios of al-lenyl alcohol and homopropargyl alcohol are 1:1.5 to 1:3.The product for reaction of phenyl propargyl bromide is allenyl alcohol and the yields are 52~84%. 相似文献
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Cheng Zhi GU Qian Rong LI Hao YIN 《中国化学快报》2005,16(12):1573-1576
Tin-indium were employed in the propargylations of various aldehydes with propargyl bromide in the presence of SnCl2 and C6H5(CH3)3NBr under microwave irradiation to afford the corresponding homopropargyl alcohols exclusively in high yields. All the reactions were completed smoothly in predominantly aqueous media in 200 seconds only. 相似文献
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《Tetrahedron: Asymmetry》2001,12(7):1063-1069
We describe a full account of our study concerning the [Cr(Salen)]-catalysed addition of propargyl halides to aldehydes. Such a procedure allows the synthesis of enantiomerically enriched homopropargyl alcohols in satisfactory yields with enantiomeric excesses (e.e.s) up to 56%. The excellent chemoselectivity for homopropargyl versus homoallenyl alcohol, represents a peculiar characteristic of our process in comparison to other chromium-mediated propargylation reactions. 相似文献
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The nucleophilic ring opening of propargyl epoxides by amines based on a silver catalyst is presented. The reaction takes place under mild conditions and features a high regioselectivity to provide an effective method for the synthesis of 2-amino homopropargyl alcohols in moderate to high yields. 相似文献
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Promoted by metallic dysprosium, carbonyl compounds react smoothly with propargyl bromide to afford the corresponding homopropargylic alcohols in good to excellent yields without observation of allenic alcohols. In addition, this reaction is regioselective and chemoselective. 相似文献
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In the presence of water, metallic tin and propargyl bromide reacted smoothly with aldehydes to give the corresponding homopropargyl alcohols (a) and homoallenyl alcohols (b). High Chemospecifity to bifounctional carbonyl compounds containing -OH, -X and -NO2 etc. was obtained. 相似文献
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Adam Shih-Yuan Lee Szu-Huio Ma Lee Yu-Ting Chang 《Research on Chemical Intermediates》2017,43(6):3493-3503
A series of 5-aryl dihydropyrrole was synthesized from the intramolecular cyclization reaction of homopropargyl amine in the presence of AgOAc as catalyst under microwave irradiation reaction conditions. The homopropargyl amine was prepared by the reaction of propargyl bromide with N-tosyl aldimine under a sonochemical Barbier-type reaction condition. Further aromatization reaction of 5-aryl dihydropyrrole in KOtBu/DMSO can afford 2-aryl pyrrole under microwave irradiation reaction conditions. 相似文献
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Promoted by metallic cadmium allylilic and propargyl bromides react smoothly with aldehydes in aqueous DMF to give homoallylic and homopropargyl alcohols in moderate to good yields. It can also promote pinacol coupling of aromatic aldehydes. The metallic cadmium is produced in situ by the reduction of CdCl2 H2O with samarium metal. 相似文献
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Trifluoromethyl aldimines reacted with acetylides in toluene at −78 °C to provide propargyl amines in good yields. From a chiral trifluoromethyl aldimine, the propargyl amines were obtained with excellent diastereoselectivities (de >98%). Trifluoromethyl propargyl amines could be further converted into difluoromethyl imines under basic conditions. 相似文献
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Papiya GhoshAngshuman Chattopadhyay 《Tetrahedron letters》2012,53(39):5202-5205
An operationally simple procedure of propargylation of aldehydes in moist solvent (distilled THF) has been developed through direct addition of propargyl bromide to aldehyde substrates mediated with low valent iron or tin. The metals were spontaneously prepared in situ employing bimetal redox strategy. Using different aldehydes as substrates (3a-k) both these metal mediated reactions took place producing homopropargyl alcohols (4a-k) in good yields in all cases and with high chemoselectivity in most of the cases (Table 1). Due to its efficacy, operational simplicity, performance in moist solvent, and being comprised of the use of inexpensive metal/metal salts, the procedure is practically viable and potentially scalable. 相似文献
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《Tetrahedron: Asymmetry》2014,25(8):658-666
A ring closing metathesis (RCM) reaction of dienes and an intramolecular Pauson–Khand (PKR) reaction of enynes derived from tertiary allyl, homoallyl, and homopropargyl alcohol backbones to afford the corresponding spirocyclic dihydrofuran and dihydropyrans and spirocyclic cyclopentenone pyrans, respectively, are described. Cyclopent-2-ene anchored tertiary allyl, homoallyl, and homopropargyl alcohols 1a–c have been efficiently resolved via enzymatic resolution with high ee (up to 90%) with 44%, 40%, and 43% chemical yields, respectively. Moreover, the cyclohex-2-ene anchored tertiary allyl, homoallyl, and homopropargyl alcohols 3a–c have also been resolved in the same manner with high ee (up to 97%) and in 42%, 45%, and 49% chemical yields. Enantiomerically enriched dienes derived from tertiary homoallyl alcohols yield the corresponding enantiomerically enriched spirocyclic dihydropyran derivatives via RCM with 74% and 78% chemical yields and with 90% and 97% ee, respectively. Moreover, enantiomerically enriched enynes derived from tertiary homoallyl alcohols afford the corresponding enantiomerically enriched cyclopentenone pyrans with spirocyclic motifs via PKR with 80% and 81% chemical yields, respectively, and as single diastereomers. 相似文献
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An enantioselective propargylation of aldehydes using an allenylzinc reagent generated in situ via a zinc-iodine exchange reaction is described. The enantioselectivity is controlled by addition of a catalytic amount of readily accessible and highly tunable amino alcohol ligand L13. A wide range of aldehydes can be propargylated to afford valuable and versatile homopropargyl alcohols in good to excellent yields with high levels of enantiopurity. 相似文献
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This paper presents Sonogashira coupling reaction of aryl bromides with protected homopropargyl alcohols such as tert-butyldimethyl(1-phenylbut-3-ynyloxy)silane
and tert-butyldimethyl(1-(2,4-dichlorophenyl)but-3-ynyloxy)silane in piperidine catalyzed by PdCl2/PPh3 without copper(I). The coupling products, disubstituted acetylene, are obtained in good or excellent yields. These products
can be further used for the synthesis of 2,5-disubstituted 3-bromofurans. 相似文献
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Reduction of secondary and tertiary o-nitrophenyl propargyl alcohols followed by acid-catalyzed Meyer-Schuster rearrangement gave 2-substituted and 2,4-disubstituted quinolines, respectively. Tertiary propargyl alcohols gave excellent yields of the quinoline derivative, while the yields of quinolines were slightly reduced when secondary propargyl alcohol derivatives were utilized. 相似文献
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Homochiral α-dibenzylamino aldehydes, prepared from the corresponding α-amino acids, react with propargyl bromide and zinc in DMF/THF (1:1) or DMF/Et2O (1:1) at 20 °C to afford, in good yields and dr, homopropargylic 1,2-amino alcohols. anti Diastereomers were always formed as major products in this reaction. These compounds are versatile intermediates for a variety of synthetic targets: γ-amino-β-hydroxy-ketones, 4-amino-1,3-diols, 1,7-diamino-2,6-diols, and ω-amino-δ-hydroxy esters. 相似文献
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The study of the reactions of tertiary propargyl alcohols with sodium halides under oxidative conditions is presented. With sodium iodide, α-iodoenones were formed, however, with sodium bromide or chloride the α-haloenones were only formed in low yields under anhydrous conditions. Conversely, upon addition of water to the reaction mixtures, α,α-dibromoketones and α,α-dichloroketones were formed in good yields, but α,α-diiodoketones were not observed. 相似文献