611187-84-9Relevant articles and documents
Formation of 1-ethenylcyclopropanols involving Kulinkovich cyclopropanation and Peterson olefination of α-trimethylsilylesters
Hazelard, Damien,Ollivier, Jean,Paugam, Renée,Salaün, Jacques
, p. 1155 - 1159 (2003)
Mercuric iodide catalyzed condensation of bis-silylketene acetals with benzaldehyde provided a 1:1 erythro and threo mixture of α-trimethylsilylesters. Only the threo adducts underwent titanium(IV)-mediated cyclopropanation and acid induced Peterson olefination to provide (Z)-1-ethenylcyclopropanols of considerable synthetic potential.
Stereospecific Synthesis of Enantioenriched Alkylidenecyclobutanones via Formal Vinylidene Insertion into Cyclopropanone Equivalents
Lindsay, Vincent N. G.,Poteat, Christopher M.
supporting information, p. 6482 - 6487 (2021/08/30)
1-Sulfonylcyclopropanols are employed here as efficient cyclopropanone equivalents in a formal vinylidene insertion process, providing the first general synthetic route to enantioenriched alkylidenecyclobutanones. The addition of an alkenyl-Grignard reage
Cobalt-Catalyzed Diastereo- and Enantioselective Hydroalkylation of Cyclopropenes with Cobalt Homoenolates
Huang, Wei,Meng, Fanke
supporting information, p. 2694 - 2698 (2020/12/03)
Catalylic diastereo- and enantioselective hydroalkylation of 3,3-disubstituted cyclopropenes with Co-homoenolate generated in situ from ring-opening of easily accessible cyclopropanols promoted by a chiral phosphine–cobalt complex is presented. Such a process represents the unprecedented and direct introduction of a wide range of functionalized alkyl groups without the need of pre-formation of stoichiometric amounts of organometallic reagents onto the cyclopropane motif, affording multi-substituted cyclopropanes in up to 99 % yield with >95:5 dr and 98:2 er. Functionalization of the products delivered enantioenriched cyclopropanes that are otherwise difficult to access.
Copper-mediated tandem ring-opening/cyclization reactions of cyclopropanols with aryldiazonium salts: Synthesis of: N -arylpyrazoles
Liu, Jidan,Xu, Erjie,Jiang, Jinyuan,Huang, Zeng,Zheng, Liyao,Liu, Zhao-Qing
supporting information, p. 2202 - 2205 (2020/02/26)
A general method for the synthesis of structurally diverse N-arylpyrazoles from readily available cyclopropanols and aryldiazonium salts is disclosed. The reaction was conducted at room temperature within minutes with a broad substrate scope and excellent regioselectivity.
Ni-Catalyzed β-Alkylation of Cyclopropanol-Derived Homoenolates
Mills, L. Reginald,Zhou, Cuihan,Fung, Emily,Rousseaux, Sophie A. L.
supporting information, p. 8805 - 8809 (2019/11/03)
Metal homoenolates are valuable synthetic intermediates which provide access to β-functionalized ketones. In this report, we disclose a Ni-catalyzed β-alkylation reaction of cyclopropanol-derived homoenolates using redox-active N-hydroxyphthalimide (NHPI) esters as the alkylating reagents. The reaction is compatible with 1°, 2°, and 3° NHPI esters. Mechanistic studies imply radical activation of the NHPI ester and 2e β-carbon elimination occurring on the cyclopropanol.
Copper-catalysed ring-opening trifluoromethylation of cyclopropanols
He, Xia-Ping,Shu, Yong-Jin,Dai, Jian-Jun,Zhang, Wen-Man,Feng, Yi-Si,Xu, Hua-Jian
supporting information, p. 7159 - 7163 (2015/07/01)
A copper-catalysed ring-opening trifluoromethylation reaction of cyclopropanols has been developed. Various β-trifluoromethyl ketones are obtained in good to excellent yields under mild reaction conditions. The present method also exhibits good functional-group compatibility. The mechanism of this new ring-opening trifluoromethylation reaction was investigated by radical trapping reactions.
Yttrium-mediated conversion of vinyl grignard reagent to a 1,2-dimetalated ethane and its synthetic application
Tanaka, Ryoichi,Sanjiki, Hiroaki,Urabe, Hirokazu
, p. 2904 - 2905 (2008/09/19)
A new 1,2-dimetalated ethane was generated from a vinyl Grignard reagent in the presence of yttrium(III) chloride, sodium cyclopentadienide, and diisobutylaluminum hydride (Dibal). This reagent enables the regio- and stereoselective (metaloethyl)metalation of acetylenes to produce ethylated alkenes after hydrolysis. In addition to simple hydrolysis, further carbon-carbon bond formation or functionalization at the metaloethyl group is possible, demonstrating that the yttrium-based 1,2-dimetalated ethane works as a conjunctive reagent. In addition, the reactive dicarbanionic character of this reagent effects one-pot synthesis of cyclopronanols from esters via consecutive double carbonyl addition. Copyright
Titanium-mediated diastereoselective formation of (E)- or (Z)-2-substituted 1-vinylcyclopropanols: Scope and limitation, applications
Racouchot, Sandrine,Sylvestre, Isabelle,Ollivier, Jean,Kozyrkov, Yuri Yu.,Pukin, Alexei,Kulinkovich, Oleg G.,Salauen, Jacques
, p. 2160 - 2176 (2007/10/03)
Titanium-mediated cyclopropanation of α,β-unsaturated esters failed to provide 1-vinylcyclopropanol derivatives in useful yields, but (E)-2-substituted-1-vinylcyclopropanols were formed diastereoselectively from O-protected β-oxo- and β-halo esters, with the allylic double bond being created subsequently (Knoevenagel condensation or dehydrohalogenation). Titanium-mediated cyclopropanation of homoallyl alk-2-enoates, on the other hand, directly provided the corresponding Z diastereomers. Palladium(0)-catalysed azidation of their sulfonic esters (tosylate, mesylate), azide reduction, and subsequent double bond cleavage afforded (E)- or (Z)-2-alkyl-2,3-methanoamino acids, although improvements are required to perform the total asymmetric syntheses of molecules with three membered-rings by these methods. Wiley-VCH Verlag GmbH, 69451 Weinheim, Germany, 2002.
Reactions of 2-substituted epichlorohydrins
Tanyeli,Demir,Akhmedov,Ozgul,Kandemir
, p. 2967 - 2980 (2007/10/03)
2-Substituted epichlorohydrins have been synthesized by starting with 1,2-dichloro acetone and various alkyl and aryl halides via dichlorohydrins followed by cyclization. The reactive 2-substituted epichlorohydrins were subjected to nucleophilic attacking of azide and cyanide ions to afford corresponding β-azido alcohols and α,β-unsaturated nitriles.
Alkylation-annulation of halo esters with organometallic reagent/SmI2 couple leading to cycloalkanols: A facile cyclopropanol synthesis from a 3-halo ester
Fukuzawa, Shin-Ichi,Furuya, Hideki,Tsuchimoto, Teruhisa
, p. 1953 - 1960 (2007/10/03)
Transformation of a 3-halo ester to cyclopropanols has been accomplished in excellent yields under mild conditions employing a coupled reagent of samarium(II) diiodide with organometallic reagents. 5- and 6-Halo esters were also transformed into cyclopentanols and cyclohexanols, respectively, in low to moderate yields. The reaction with a 4-halo ester gave 2,2-disubstituted tetrahydrofuran as a major product that resulted from double alkylation followed by cyclization; a substituted cyclobutanol was formed in poor yield.
