Organic Letters

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ISSN / EISSN : 1523-7060 / 1523-7052
Published by: American Chemical Society (ACS) (10.1021)
Total articles ≅ 34,325
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Sheng-Rong Guo, Yan-Qin Yuan, Jian-Nan Xiang
Organic Letters; doi:10.1021/acs.orglett.1c01680

Mohanan Biji, , Ravi S. Lankalapalli
Organic Letters; doi:10.1021/acs.orglett.1c01997

Photoirradiation of (6E,9E)-zerumbone-2,3-epoxide afforded a diverse range of transannular cyclized products in the presence of a catalytic amount of Sc(OTf)3. At the behest of the geometrical isomers produced by photoirradiation, the diversity encompasses an unprecedented eudesmane core and oxo-bridged hydroxy-olefin skeletons. Structure elucidation and the stereochemical outcome of the products are described via extensive NMR analysis. The present study serves as a model for tandem photoisomerization and transannular cyclization of natural products with enone/dienone functionality.
Naoki Sakai, Kyohei Kawashima, Masashi Kajitani, , Takeshi Oriyama
Organic Letters; doi:10.1021/acs.orglett.1c01831

Maleimides are often used as electrophiles in conventional reactions; however, their application as nucleophiles is limited to only a few reactions, and reactions utilizing α-aminomaleimides as asymmetric Michael donors have not been reported to date. Thus, in this work, asymmetric Michael addition of α-aminomaleimides as Michael donors to β-nitrostyrenes was conducted for the first time using an organocatalyst derived from a Cinchona alkaloid. Density functional theory investigations were crucial to improve the enantioselectivity of the adduct.
Guanming Liao, Xing Chen, Yali Qiao, Kanglei Liu, , ,
Organic Letters; doi:10.1021/acs.orglett.1c01983

A series of dicyanomethylene-functionalized triarylboranes is reported in this work, with low-lying LUMO energy levels at ca. −3.66 eV for FMesB-ACN. The single-crystal structures of the mono- and dianion of Mes*B-ACN were obtained via chemical reduction, which revealed a conversion from a quinoidal to an aromatic structure. The strong Lewis acidity of these compounds is reflected in a fluoride-anion binding experiment. This work introduces a facile strategy for modulating the electron deficiency of boron-containing compounds.
, Guo Yu, Wenwu Li, Zhigang Shu, Longyu Wang, Zhaoting Li, Xia Gao
Organic Letters; doi:10.1021/acs.orglett.1c01985

An unprecedented copper-catalyzed multicomponent radical-based reaction involving alkenes, P(O)H compounds, sulfur powder, and Togni reagent II at room temperature has been developed. A variety of highly functionalized CF3-containing S-alkyl phosphorothioates can be directly prepared from a wide range of activated and unactivated alkenes. Moreover, this protocol highlights its potential in the late-stage functionalization of complex molecules and opens up a new avenue for the construction of C(sp3)–S–P bonds.
Organic Letters; doi:10.1021/acs.orglett.1c01953

This work describes the application of pentafluoropyridine (PFP), a cheap commercially available reagent, in the deoxyfluorination of carboxylic acids to acyl fluorides. The acyl fluorides can be formed from a range of acids under mild conditions. We also demonstrate that PFP can be utilized in a one-pot amide bond formation via in situ generation of acyl fluorides. This one-pot deoxyfluorination amide bond-forming reaction gives ready access to amides in yields of ≤94%.
Ling Dai, Shuling Yu, , Xuanzeng Ye, , Zhongyan Chen,
Organic Letters; doi:10.1021/acs.orglett.1c01762

We herein report an efficient approach for the assembly of multiply substituted imidazoles and oxazoles in a single-step manner. These transformations are based on a decarboxylation addition and annulation of readily accessible aromatic carboxylic acids and aliphatic nitriles and exhibit good functional group compatibility and a high step economy. The reaction is scalable, and as-prepared products could be transformed into practical skeletons. Importantly, the late-stage derivatization of Momelotinib highlights the potential utility of this methodology.
Ya-Nan Ding, Yan-Chong Huang, Wei-Yu Shi, Nian Zheng, Cui-Tian Wang, Xi Chen, Yang An, Zhe Zhang,
Organic Letters; doi:10.1021/acs.orglett.1c01723

We described a novel palladium-catalyzed domino procedure for the preparation of (hetero)aryl thio/selenoglycosides. Readily available (hetero)aryl iodides and easily accessible 1-thiosugars/1-selenosugars are utilized as the substrates. Meanwhile, 10 types of sugars are quite compatible with this reaction with good regio- and stereoselectivity, high efficiency, and broad applicability (up to 89%, 53 examples). This method enables the straightforward formation of the C(sp2)–S/Se bond of (hetero)aryl thio/selenoglycosides.
Vasiliy M. Muzalevskiy, Zoia A. Sizova,
Organic Letters; doi:10.1021/acs.orglett.1c02061

The reaction of α-CF3-β-(2-nitroaryl)enamines with benzaldehydes led to nitro-substituted α,β-diaryl-CF3-enones in high yield. Subsequent reduction of the nitro-group to the amino moiety by the Pd/C-NH4HCO2 system resulted in intramolecular cyclization to form a 5-membered hemiaminal which is stabilized by the presence of a CF3-group. The reaction of this hemiaminal with various nucleophiles afforded functionalized 2-CF3-indoles isolated in up to quantitative yields. High efficiency and broad synthetic scope of all steps of the sequence were demonstrated. A possible mechanism of the reaction is discussed.
Victor Adebomi, Mahesh Sriram, Xavier Streety, Monika Raj
Organic Letters; doi:10.1021/acs.orglett.1c01622

Here we solve a long-standing challenge of the site-selective modification of secondary amides and present a simple two-step, metal-free approach to selectively modify a particular secondary amide in molecules containing multiple primary and secondary amides. Density functional theory (DFT) provides insight into the activation of C–N bonds. This study encompasses distinct chemical advances for late-stage modification of peptides thus harnessing the amides for the incorporation of various functional groups into natural and synthetic molecules.
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