194805-72-6Relevant academic research and scientific papers
Preparation of conjugated dienoates with Bestmann ylide: Towards the synthesis of zampanolide and dactylolide using a facile linchpin approach
Wang, Jingjing,Ting, Samuel Z. Y.,Harvey, Joanne E.
supporting information, p. 1815 - 1822 (2016/04/10)
Bestmann ylide [(triphenylphosphoranylidene)ketene] acts as a chemical linchpin that links nucleophilic entities, such as alcohols or amines, with carbonyl moieties to produce unsaturated esters and amides, respectively. In this work, the formation of α,β
Copper-Catalyzed Oxy-Alkenylation of Homoallylic Alcohols to Generate Functional syn-1,3-Diol Derivatives
Holt, Dean,Gaunt, Matthew J.
supporting information, p. 7857 - 7861 (2015/06/30)
A novel method for the synthesis of a wide range of functionalized 1,3-diol derivatives is reported. Employing a copper-catalyzed oxy-alkenylation strategy, a range of readily available, substituted homoallylic alcohol derivatives and alkenyl(aryl) iodonium salts combine to form syn-1,3-carbonates in excellent yield and with high selectivity. Furthermore, the products formed are amenable to an iterative reaction sequence, thus affording highly complex polyketide-like fragments. Polyols: The reported copper-catalyzed oxy-alkenylation strategy works well for a range of readily available, substituted homoallylic alcohol derivatives and alkenyl(aryl) iodonium salts to form syn-1,3-carbonates in excellent yield and high selectivity. Furthermore, the products formed are amenable to an iterative reaction sequence, thus affording highly complex polyketide-like fragments.
Catalytic synthesis of enantiopure mixed diacylglycerols-synthesis of a major M. tuberculosis phospholipid and platelet activating factor
Fodran, Peter,Minnaard, Adriaan J.
supporting information, p. 6919 - 6928 (2013/10/08)
An efficient catalytic one-pot synthesis of TBDMS-protected diacylglycerols has been developed, starting from enantiopure glycidol. Subsequent migration-free deprotection leads to stereo- and regiochemically pure diacylglycerols. This novel strategy has been applied to the synthesis of a major Mycobacterium tuberculosis phospholipid, its desmethyl analogue, and platelet activating factor.
Hexafluoroisopropanol as a unique solvent for stereoselective lododesilylation of vinylsilanes
Ilardi, Elizabeth A.,Stivala, Craig E.,Zakarian, Armen
supporting information; experimental part, p. 1727 - 1730 (2009/04/10)
Stereoselective preparation of iodoalkenes from vinylsilanes is described. 1,1,1,3,3,3-Hexafluoroisopropanol serves as a unique solvent that ensures high yields and stereoselectivities in the iododesilylation of a variety of functionalized substrates.
Phosphonyl radical addition to enol ethers. The stereoselective synthesis of cyclic ethers
Jessop, Christopher M.,Parsons, Andrew F.,Routledge, Anne,Irvine, Derek J.
, p. 5095 - 5098 (2007/10/03)
Addition of diethyl phosphite or diethyl thiophosphite to enol ethers, in the presence of a radical initiator, results in the regioselective synthesis of organophosphonate or phosphonothioate derivatives, respectively, under mild conditions. This method c
Stereoselective synthesis of cyclic ethers by intramolecular trapping of dicobalt hexacarbonyl-stabilized propargylic cations
Betancort, Juan M.,Martin, Tomas,Palazon, Jose M.,Martin, Victor S.
, p. 3216 - 3224 (2007/10/03)
The intramolecular attack of a hydroxy group on an exo-biscobalthexacarbonyl propargylic cation provides cyclic ethers with six- to nine-membered rings. The scope and limitations of the methodology are described. The reaction is stereoselective when addit
Room-temperature metallation of 2-substituted 1,3-dithiane derivatives and subsequent coupling with 2,3-disubstituted oxiranes
Ide, Mitsuaki,Nakata, Masaya
, p. 2491 - 2499 (2007/10/03)
2-Substituted 1,3-dithiane derivatives, (S)-1(t-butyldiphenylsiloxy)-2- (1,3-dithian-2-yl)propane (9), (S)-1-(t-butyldimethylsiloxy)-2-(1,3-dithian- 2-yl)propane, 1-(t-butyldiphenylsiloxy)-2-(1,3-dithian-2-yl)-2-methylpropane, and 1,2-bis-(t-butyldiphenylsiloxy)-3-(1,3-dithian-2-yl)propane, were subjected to lithiation in THF with n-BuLi at room temperature (r.t.); the resulting anions reacted with 2,3-disubstituted oxirane, trans-2-methyl-3- (triphenylmethoxymethyl)oxirane(22), at r.t., giving the coupling products in satisfactory yield. On the other hand, the lithium salt formed in ether from (S)2-(1,3-dithian-2-yl)-1-(4-methoxybenzyloxy)propane with n-BuLi at r.t. reacted with 22 at r.t. in the presence of hexamethylphosphoric triamide to afford the coupling product in moderate yield. In addition, a mixed organometallic reagent, n-BuLi/Bu2Mg, was found to be an effective metallation reagent for 9 and the resulting anion reacted with 22 to afford the coupling product in good yield.
Asymmetric synthesis of oxazolidine nucleosides and related chemistry
Du, Jinfa,Chu, Chung K.
, p. 1 - 13 (2007/10/03)
Asymmetric synthesis of N-substituted oxazolidinyl nucleosides has been accomplished from L-isoserine. trans- and cis-Oxazolidine intermediates (4 and 5) were stereoselectively constructed from N-protected L-isoserine with a menthoxycarbonyl group by the condensation with benzoyloxy acetaldehyde dimethyl acetal in a ratio of 3.9 to 1 in favor of trans-isomer 4. The major isomer 4 was converted to enantiomerically pure β- and α- N-L- menthoxycarbonyl oxazolidinyl thymine nucleosides 11 and 12 in 6 steps.
