177606-52-9Relevant academic research and scientific papers
Addition of vinylmetallic reagents to chiral 2-formyltetrahydrofuran
Lamariano-Merketegi, Janire,Lorente, Adriana,Gil, Alejandro,Albericio, Fernando,lvarez, Mercedes
, p. 235 - 241 (2015)
Polyketide macrolides, which belong to an interesting family of metabolites, are complex structures with valuable bioactivity. In this work, several procedures for the bond formation between a vinylorganometallic reagent and a chiral formyl-THF compound were examined for the subsequent application to the total synthesis of phormidolides. Model molecules were synthesized to study and optimize the method that mimics the union of the polyhydroxy chain with the macrocycle of the target polyketide macrolides. A chelation-controlled organometallic addition, a carboalumination, and the Nozaki-Hiyama-Kishi (NHK) reaction were the three chosen reactions to investigate this bond formation. Satisfactory diastereoselectivity and yields were obtained.
NiH-Catalyzed Migratory Defluorinative Olefin Cross-Coupling: Trifluoromethyl-Substituted Alkenes as Acceptor Olefins to Form gem-Difluoroalkenes
Chen, Fenglin,He, Yuli,Huang, Genping,Xu, Xianfeng,Zhu, Shaolin
supporting information, p. 5398 - 5402 (2020/02/28)
We report a NiH-catalyzed migratory defluorinative coupling between two electronically differentiated olefins. A broad range of unactivated donor olefins can be joined directly to acceptor olefins containing an electron-deficient trifluoromethyl substituent in both intra- and intermolecular fashion to form gem-difluoroalkenes. This migratory coupling shows both site- and chemoselectivity under mild conditions, with the formation of a tertiary or quaternary carbon center.
TRICYCLIC HETEROCYCLE COMPOUNDS USEFUL AS HIV INTEGRASE INHIBITORS
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Page/Page column 21-22; 35, (2019/11/12)
The present invention relates to Tricyclic Heterocycle Compounds of Formula (I): (I) and pharmaceutically acceptable salts or prodrug thereof, wherein R1, R2, R3, R4, R5, R6 and n are as defined herein. The present invention also relates to compositions comprising at least one Tricyclic Heterocycle Compound, and methods of using the Tricyclic Heterocycle Compounds for treating or preventing HIV infection in a subject.
Chemo-, regio-, and stereo-selective perfluoroalkylations by a Grignard complex with zirconocene
Fujiu, Motohiro,Negishi, Kazuyuki,Guang, Jie,Williard, Paul G.,Kuroki, Shigeki,Mikami, Koichi
supporting information, p. 19464 - 19468 (2015/11/27)
The synthesis of highly reactive perfluoroalkyl Grignard reagents with early transition metal zirconocene complexes and their new types of highly chemo-, regio-, and stereo-selective perfluoroalkylation reactions are reported with epoxides in particular. The zirconocene complex is advantageous in activating the perfluoroalkyl Grignard species. The zirconocene·Grignard complexes were clarified by DOSY. Both 1H and 19F DOSY analyses show that the addition of MAO and dioxane to the mixture of RFMgCl and Cp2ZrCl2 connects Cp2Zr and RFMg to generate the zirconocene/perfluoroalkyl-Grignard/dioxane complex.
Stereoselective alkene isomerization over one position
Larsen, Casey R.,Grotjahn, Douglas B.
supporting information; experimental part, p. 10357 - 10360 (2012/08/08)
Although controlling both the position of the double bond and E:Z selectivity in alkene isomerization is difficult, 1 is a very efficient catalyst for selective mono-isomerization of a variety of multifunctional alkenes to afford >99.5% E-products. Many reactions are complete within 10 min at room temperature. Even sensitive enols and enamides susceptible to further reaction can be generated. Catalyst loadings in the 0.01-0.1 mol% range can be employed. E-to-Z isomerization of the product from diallyl ether was only -6 times as fast as its formation, showing the extremely high kinetic selectivity of 1.
Syntheses of the four stereoisomers of Phytophthora mating hormone α2 and a concise synthesis of mating hormone α1
Yajima, Arata,Toda, Kou,Molli, Shylaja D.,Ojika, Makoto,Nukada, Tomoo
experimental part, p. 8887 - 8894 (2011/12/14)
Four stereoisomers of Phytophthora mating hormone α2 were synthesized using both enantiomers of citronellol as starting materials. The absolute configuration of the natural product was determined to be 7S,11R,15R by oospore-inducing assays of the syntheti
Syntheses of seven-membered rings: Ruthenium-catalyzed intramolecular [5+2] cycloadditions
Trost, Barry M.,Shen, Hong C.,Horne, Daniel B.,Toste, F. Dean,Steinmetz, Bernhard G.,Koradin, Christopher
, p. 2577 - 2590 (2007/10/03)
The Ru-catalyzed intramolecular [5+2] cycloaddition of cyclopropylenynes is investigated with respect to the regio- and diastereoselectivity as well as the functional group compatibility of the reaction. Evidence for the mechanism as occurring through a ruthenacyclopentene intermediate is elucidated from 1) the study of the diastereoselectivity of the cycloaddition; 2) the effect of variation of substituents on the regioselectivity of cyclopropyl bond cleavage in 1,2-trans- and 1,2-cis-disubstituted cyclopropanes and 3) examples that clearly do not involve ruthenacyclohexene as intermediates as products still incorporate the cyclo propyl moiety. The scope and limitations of the Ru-catalyzed cycloaddition are discussed and compared with the Rh-catalyzed reaction. The potential power of this methodology towards natural product total synthesis is demonstrated by the formation of several polycyclic systems with the chosen reaction conditions and readily available cyclopropylenyne substrates.
Direct preparation of allylstannanes from allyl alcohols: Convenient synthesis of β-substituted allylstannanes and of stereodefined γ-substituted allylstannanes
Weigand, Stefan,Brueckner, Reinhard
, p. 475 - 482 (2007/10/03)
Primary allyl alcohols are converted into allyltributylstannanes in a one-pot operation. It entails (i) deprotonation with BuLi, (ii) sulfonylation with mesyl chloride, and (iii) nucleophilic substitution by LiSnBu3. Conversions are quantitative with isolated yields ranging from 70% to 100%. If the starting allyl alcohol contains a stereogenic double bond its configuration is retained.
