56068-50-9Relevant academic research and scientific papers
Enantioselective "clip-cycle" synthesis of di-, tri- and spiro-substituted tetrahydropyrans
Alomari, Khadra,Sai Pavan Chakravarthy,Duchadeau, Bastien,Ermanis, Kristaps,Clarke, Paul A.
supporting information, p. 1181 - 1185 (2022/02/19)
ω-Unsaturated alcohols were "clipped"via alkene metathesis to a thioester activating group, which was followed by a chiral phosphoric acid catalyzed intramolecular oxa-Michael cyclization to yield tetrahydropyrans and spiro-tetrahydropyrans with excellent
Tuning the Reactivity of Alkoxyl Radicals from Cyclization to 1,2-Silyl Transfer: Stereoselective Synthesis of β-Substituted Cycloalcohols
He, Xingyi,Shen, Xiao,Zhang, Zeguo,Zhao, Yunlong
supporting information, (2022/03/17)
Herein, we report a radical strategy for diastereoselective construction of β-substituted cyclopentanols and cyclobutanols. The success of the reaction is attributed to the favorable radical 1,2-silyl transfer over the cyclization of alkoxy radicals to the olefins. The reaction shows broad substrate scope and wide functional-group tolerance. The synthetic potential of the methodology was demonstrated in the gram scale reaction and facile synthesis of various spiro compounds.
Enantio- and Regioselective Palladium(II)-Catalyzed Dioxygenation of (Aza-)Alkenols
Giofrè, Sabrina,Molteni, Letizia,Nava, Donatella,Lo Presti, Leonardo,Beccalli, Egle Maria
supporting information, p. 21723 - 21727 (2021/09/08)
An oxidative Pd-catalyzed intra-intermolecular dioxygenation of (aza-)alkenols has been reported, with total regioselectivity. To study the stereoselectivity, different chiral ligands as well as different hypervalent-iodine compounds have been compared. I
Rhodium-Catalyzed Cyclization of O,ω-Unsaturated Alkoxyamines: Formation of Oxygen-Containing Heterocycles
Escudero, Julien,Bellosta, Véronique,Cossy, Janine
supporting information, p. 574 - 578 (2018/02/21)
O,ω-Unsaturated N-tosyl alkoxyamines undergo unexpected RhIII-catalyzed intramolecular cyclization by oxyamination to produce oxygen-containing heterocycles. Mechanistic studies show that an aziridine intermediate seems to be responsible for the formation of the heterocycles, possibly via a RhV species.
Ring-opening of cyclic ethers with carbon-carbon bond formation by Grignard reagents
Christensen, Stig Holden,Holm, Torkil,Madsen, Robert
, p. 4942 - 4946 (2014/07/07)
The ring-opening of cyclic ethers with concomitant C-C bond formation was studied with a number of Grignard reagents. The transformation was performed in a sealed vial by heating to ~160 °C in an aluminum block or at 180 °C in a microwave oven. Good yields of the product alcohols were obtained with allyl- and benzylmagnesium halides when the ether was tetrahydrofuran or 3,3-dimethyloxetane. Lower yields were obtained with substituted tetrahydrofurans while no ring-opening was observed with tetrahydropyran. Only highly reactive allyl and benzyl Grignard reagents participated in the transformation while no reaction occurred with other alkylmagnesium halides.
BISMACROKYCLIC COMPOUNDS AS HEPATITIS C VIRUS INHIBITORS
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Page/Page column 92, (2011/05/06)
The present invention discloses compounds of formula (Ia) or (Ib) or pharmaceutically acceptable salts, esters, or prodrugs thereof: which inhibit serine protease activity, particularly the activity of hepatitis C virus (HCV) NS3-NS4A protease. Consequent
Synthesis of vaniprevir (MK-7009): Lactamization to prepare a 22-membered macrocycle
Song, Zhiguo J.,Tellers, David M.,Journet, Michel,Kuethe, Jeffrey T.,Lieberman, David,Humphrey, Guy,Zhang, Fei,Peng, Zhihui,Waters, Marjorie S.,Zewge, Daniel,Nolting, Andrew,Zhao, Dalian,Reamer, Robert A.,Dormer, Peter G.,Belyk, Kevin M.,Davies, Ian W.,Devine, Paul N.,Tschaen, David M.
experimental part, p. 7804 - 7815 (2011/12/14)
Development of a practical synthesis of MK-7009, a 22-membered macrocycle, is described. A variety of ring-closing strategies were evaluated, including ring-closing metathesis, intermolecular palladium-catalyzed cross-couplings, and macrolactamization. Ri
MASKED CARBOXYLATE NEOPENTYL SULFONYL ESTER CYCLIZATION RELEASE PRODRUGS OF ACAMPROSATE, COMPOSITIONS THEREOF, AND METHODS OF USE
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Page/Page column 54, (2009/04/24)
Masked carboxylate neopentyl sulfonyl ester prodrugs of acamprosate, pharmaceutical compositions comprising such prodrugs, and methods of using such prodrugs and compositions thereof for treating diseases are disclosed. In particular, acamprosate prodrugs
Cobalt-catalysed hydrovinylation as the key step in a short synthesis of moenocinol
Hilt, Gerhard,Treutwein, Jonas
supporting information; experimental part, p. 1395 - 1397 (2009/07/10)
A regio- and chemoselective cobalt(i)-catalysed 1,4-hydrovinylation reaction is the key step in the straightforward and convergent synthesis of moenocinol, the aglycone of moenomycin A.
A relay ring-closing metathesis synthesis of dihydrooxasilines, precursors of (Z)-lodo olefins
Xie, Qiuzhe,Denton, Richard W.,Parker, Kathlyn A.
supporting information; experimental part, p. 5345 - 5348 (2009/06/06)
(Chemical Equation Presented) A convenient Grubbs II metathesis provides dihydrooxasilines by relay RCM (RRCM). Dihydrooxasilines undergo ring opening to give Z-vinyl silanes. These can then be converted to Z-vinyl iodides. This sequence provides a short,
