14004-19-4Relevant academic research and scientific papers
Z Stereoselective Wittig Olefination of 2-Oxygenated Cyclohexanones
Koreeda, Masato,Patel, Paresh D.,Brown, Lindsey
, p. 5910 - 5912 (1985)
Protected 2-hydroxy- and 2,3-epoxycyclohexanones provided (Z)-ethylidenecyclohexanes in a highly stereoselective manner upon their reactions with ethylidenetriphenylphosphorane in both the lithium base and the lithium-free conditions of the Wittig reactio
Synthesis of benzofurans from the cyclodehydration of α-phenoxy ketones mediated by Eaton’s reagent
Ma, Lin,Ma, Zhanwei,Zhang, Min,Zhou, Min
, p. 426 - 436 (2020/03/23)
Cyclodehydration of α-phenoxy ketones promoted by Eaton’s reagent (phosphorus pentoxide–methanesulfonic acid) is used to prepare 3-substituted or 2,3-disubstituted benzofurans with moderate to excellent yields under mild conditions. The method provides a facile access to benzofurans from readily available starting materials such as phenols and α-bromo ketones. The reaction is highly efficient, which is attributed to the good reactivity and fluidity of Eaton’s reagent. The reaction can be applied to prepare naphthofurans, furanocoumarins, benzothiophenes, and benzopyrans.
Titanium tetrachloride promoted cyclodehydration of aryloxyketones: Facile synthesis of benzofurans and naphthofurans with high regioselectivity
Zhang, Qiu,Luo, Juan,Wang, Bingqiao,Xiao, Xiaoqin,Gan, Zongjie,Tang, Qiang
supporting information, p. 1337 - 1340 (2019/04/16)
An efficient and facile method for the synthesis of a broad series of benzofurans and naphthofurans is described. The direct intramolecular cyclodehydration of aryloxyketones in the presence of titanium tetrachloride affords the corresponding benzofurans and naphthofurans with good regioselectivity and yields.
Simplified procedure for TEMPO-catalyzed oxidation: Selective oxidation of alcohols, α-hydroxy esters, and amides using TEMPO and calcium hypochlorite
Reddy, Sabbasani Rajasekhara,Stella, Selvaraj,Chadha, Anju
experimental part, p. 3493 - 3503 (2012/09/22)
A wide range of primary and secondary multifunctional alcohols, α-hydroxyamides, and α-hydroxyesters were oxidized to their corresponding aldehydes, ketones, α-ketoamides, and α-ketoesters under mild reaction conditions using 2,2,6,6-tetramethylpiperidine-1-oxyl as a catalyst with calcium hypochlorite as an oxidant [TEMPO-Ca(OCl)2]. This simplified method does not require any transition metals, acids, or bases and demonstrates controlled and selective oxidation of structurally diverse alcohols, affording moderate to excellent yields at room temperature.
Enantioselective synthesis of chiral β-aryloxy alcohols by ruthenium-catalyzed ketone hydrogenation via dynamic kinetic resolution (DKR)
Bai, Wen-Ju,Xie, Jian-Hua,Li, Ya-Li,Liu, Sheng,Zhou, Qi-Lin
supporting information; experimental part, p. 81 - 84 (2010/06/16)
A highly efficient enantioselective synthesis of chiral β-aryloxy alcohols by the [RuCl2[(S)-SDP][(R, R)-DPEN]} [(Sa,R, R)-1a; SDP = 7, 7′-bis-(diarylphosphino)-1,1′-spirobiindane; DPEN = trans-1,2-diphenylethylenediamine] complex-ca
Nucleophilic substitution reactions of sulfur-substituted cyclohexanone acetals: An analysis of the factors controlling stereoselectivity
Billings, Susan B.,Woerpel
, p. 5171 - 5178 (2007/10/03)
The reactions of cyclohexanone acetals substituted with thiophenyl groups (and other heteroatoms) at C-2 demonstrate the powerful influence that these substituents have on the stereoselectivity of nucleophilic substitution reactions. The trans selectivities of these reactions correlate with the behavior of the corresponding ketones. These experiments lend support to the possibility that the reactions of the acetals, which proceed via oxocarbenium ions, are operating under Felkin-Anh control.
Hydroxamic acid compounds useful as matrix metalloproteinase inhibitors
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Page column 22, (2008/06/13)
Compounds of the formula; are useful for inhibiting matrix metalloproteinase enzymes in animals, and as such, prevent and treat diseases resulting from the breakdown of connective tissues. Also disclosed are methods for the preparation of such compounds,
Tricyclic biphenyl sulfonamide matrix metalloproteinase inhibitors
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Page 11, (2008/06/13)
Matrix metalloproteinase inhibitors are tricyclicsulfonamides of the Formula I or a pharmaceutically acceptable salt thereof, wherein R1 and R2 include hydrogen, alkyl, and substituted alkyl; R3 is OH or NHOH; X is O or S(
Diastereo- and enantioselective synthesis of cis-2- hydroxycyclohexanamine and corresponding ethers by asymmetric reductive amination
Lauktien, Gerhard,Volk, Franz-J,Frahm, August W.
, p. 3457 - 3466 (2007/10/03)
A series of homochiral cis-2-alkoxy- and 2-aryloxyeyclohexanamines 5b- 5e has been synthesised by means of asymmetric reductive amination of the corresponding racemic 2-oxygenated cyclohexanones 2 with ee-values ranging from 95 to >99%. The respective 2-hydroxy and 2-cyclohexyl derivatives 5g-5h have been prepared from the 2-phenoxycyclohexanamine 4e. Relative and absolute stereochemistry has been elucidated.
Synthesis of 3-arylidene and 3-cyclohexylidene benzofuran-2(3H)-ones via Claisen rearrangement
Balakumar, Arumugham,Janardhanam, Selvasekaran,Rajagopalan, Krishnamoorthy
, p. 313 - 317 (2007/10/02)
Claisen rearrangement of aryl-allyl ethers bearing substituents on the allylic portion of the substrate have been reported to yield very interesting products. α-Aryloxymethyl cinnamates furnish 3-benzylidene and 3-benzylcoumarins after isomerisation while
