Science China Chemistry, Год журнала: 2024, Номер unknown
Опубликована: Сен. 9, 2024
Язык: Английский
Science China Chemistry, Год журнала: 2023, Номер 67(2), С. 595 - 603
Опубликована: Окт. 23, 2023
Язык: Английский
Процитировано
8
Advanced Synthesis & Catalysis, Год журнала: 2024, Номер 366(9), С. 2014 - 2019
Опубликована: Март 18, 2024
Abstract Creating an expedient method for synthesizing biologically significant functionally rich octahydroquinoline is a highly sought‐after yet challenging endeavour. In this report, we document unprecedented approach to the construction of novel spirooctahydroquinoline oxindole architectures. The reaction proceeds through Pd (II) catalyzed cycloisomerisation and quinine [4+2]‐addition sequence afford desired adduct in moderate excellent yield (up 89%) single diastereomer with three contiguous stereocenters including one spirocenter. An overwhelming number libraries were generated (35 examples) reflecting synthetic versatility functional groups/substituents tolerance. Further, transformed into medicinally important fluoro‐decahydroepoxyethanoquinoline spirooxindole scaffold five selectivity (95% >99:1 dr) steps which signifies utility developed methodology.
Язык: Английский
Процитировано
1
Organic Chemistry Frontiers, Год журнала: 2024, Номер 11(11), С. 3072 - 3079
Опубликована: Янв. 1, 2024
A three-component Friedel–Crafts type difunctionalization of ynamides with an iodine( iii ) electrophile and electron-rich (hetero)arenes has been developed, enabling regio- stereoselective synthesis densely functionalized enamides.
Язык: Английский
Процитировано
1
The Journal of Organic Chemistry, Год журнала: 2024, Номер 89(9), С. 6274 - 6280
Опубликована: Апрель 20, 2024
Herein, a one-pot desulfonylative protocol enabled by copper(II)/zinc(II) salts to access pyrrolo[2,3-b]quinolines in good excellent yields from 2-carbonylanilines and ynamide-derived buta-1,3-diynes has been reported. Significantly, various carrying reactive functional groups are well tolerated. Moreover, gram-scale synthesis synthetic application highlight the practical utility of current protocol. Notably, fluorescence properties have recorded, their potential use as fluorescent probe imaging live cells demonstrated.
Язык: Английский
Процитировано
1
The Journal of Organic Chemistry, Год журнала: 2024, Номер 89(13), С. 9695 - 9699
Опубликована: Июнь 19, 2024
UV light-promoted synthesis of α-sulfonyl amides from N-sulfonyl ynamides without any additives is reported. The reaction proceeds through a radical chain mechanism involving the photoinduced cleavage nitrogen–sulfur bond and addition an electrophilic sulfonyl to triple ynamide followed by β-fragmentation group leading ketenimine hydrated upon workup. This highly efficient rearrangement leads, after acidic treatment, wide range in high yields.
Язык: Английский
Процитировано
1
The Journal of Organic Chemistry, Год журнала: 2024, Номер 89(16), С. 11455 - 11466
Опубликована: Авг. 6, 2024
The synthesis of stereodefined tetrasubstituted alkenes bearing four different functional groups is challenging. Herein, we disclose a 100% atom-economic and highly regio- stereoselective halo-chalcogenations, in particular, chlorosulfenylation, bromosulfenylation, chloroselenation, bromoselenation, ynamides toluene at room temperature under an aerobic atmosphere for the wide variety excellent yields. Notably, all reactions are efficient furnished desired products yield (average >96%) stereoselectivity (
Язык: Английский
Процитировано
1
The Journal of Organic Chemistry, Год журнала: 2024, Номер 89(17), С. 12439 - 12451
Опубликована: Авг. 9, 2024
We disclose a sustainable and versatile synthetic strategy for the highly chemo-, regio-, stereoselective hydrofunctionalizations of ynamides, through its activation by solvent, HFIP, to access wide variety stereodefined ketene N,N, N,O, N,S, N,Se acetals in high yield at room temperature. The reaction proceeded formation reactive keteniminium ion intermediate, formed via protonation β-carbon ynamide followed an attack nucleophile (syn-addition) α-carbon. When ynamides are treated with only HFIP temperature, addition products 100% atom-economic fashion; however, presence stronger N-/O-/S-/Se-based nucleophile, corresponding syn-hydroheterofunctionalized formed. Notably, played multiple roles, such as reagent, particular, Brønsted acid, well solvent. Interestingly, is found be unique this transformation. utilized late-stage functionalization several marketed drugs natural products, it also enables connection two different or drug product chemical bonds. Significantly, was recovered after reused consecutive reactions.
Язык: Английский
Процитировано
1
Organic Chemistry Frontiers, Год журнала: 2024, Номер 11(24), С. 7168 - 7175
Опубликована: Янв. 1, 2024
The regioselective hydro-functionalization reaction is a powerful method to convert readily available alkynes into structurally diverse olefins.
Язык: Английский
Процитировано
1
Organic & Biomolecular Chemistry, Год журнала: 2023, Номер 21(28), С. 5737 - 5741
Опубликована: Янв. 1, 2023
A Pd( ii ) catalyzed syn -symmetrical diarylation of ynamides has been showcased utilizing readily available arylboronic acids as nucleophilic arylating agents.
Язык: Английский
Процитировано
3
Advanced Synthesis & Catalysis, Год журнала: 2024, Номер 366(6), С. 1298 - 1305
Опубликована: Янв. 26, 2024
Abstract The rhodium‐catalyzed hydroformylation of alkynyl sulfides at 40 °C under 5 bars syngas is described. method gives access to α‐sulfenyl acroleins with α/β regioselectivities up 89/11 and applicable alkyl or aryl substituted substrates. It effective even on more complex substrates, such as cysteine cholesterol derivatives. To demonstrate the synthetic potential obtained products, ( Z )‐3‐cyclohexyl‐2‐methylsulfenyl acrolein was selected an example its sulfur atom selectively oxidized corresponding sulfoxide sulfone. Acid‐promoted ) E isomerization double bond occurred during oxidation. three sulfenyl‐, sulfinyl‐, sulfonyl‐functionalized have been then used dienophiles cyclohexene carbaldehydes.
Язык: Английский
Процитировано
0