The dearomative [5 + 1] annulation of 2-methylindoles with new five-membered synthon was developed through cascade [1,5]-hydride transfer/dearomative cyclization in HFIP for the synthesis of spirochromanes bearing the 2-methylindolenine skeleton.
An aromatization-driven hydride transfer-involved α-C(sp3)–H bond functionalization of the oxygen atom was developed. Easily prepared p-quinone methides were applied to initiate [1,5]-hydride transfer/cyclization for generating spirochromanes.
Isoxazolines are highly significant for the development of new synthetic methodology and pharmaceutics. Indolines and 2,3dihydrobenzofurans are also privileged structures in natural products and pharmaceuticals. In continuation of our ongoing research on transformations of 5-aminoisoxazoles and quinone derivaties, herein we report Sc(OTf) 3 -catalyzed dearomative [3 + 2] annulations of 5-aminoisoxazoles with quinone imine ketals (QIKs) and quinone monoacetals (QMAs). A variety of indolineand 2,3-dihydrobenzofuran-fused isoxazolines were afforded in moderate to good yields with excellent diastereoselectivities (all cases > 20 : 1 dr). This method featured mild reaction conditions, wide substrate scope, and gram-scale synthesis.
An enantioselective addition of 5-amino-isoxazoles with β,γ-alkynyl-α-ketimino esters catalyzed by a chiral phosphoric acid has been developed. This procedure allowed the formation of quaternary α-isoxazole-α-alkynyl amino acid derivatives with high...
Isothiazole units exist in many natural products and pharmaceutics. Up to now, construction of isothiazolecontaining axially chiral biaryls has not been reported yet. Herein we disclose a chiral phosphoric acid catalyzed atropoenantioselective arylation of 5-amino-isothiazoles with methyl p-quinone carboxylate. Various novel isothiazole-[a] Y.
An enantioselective intramolecular Pictet-Spengler type annulation of indole-linked 3-methyleneisoindolin-1-ones was developed by using a chiral phosphoric acid as catalyst. This method enabled the construction of a series of chiral isoindolinone...
A tandem reaction of phenyl α‐cyano‐α‐arylacetates with quinone monoimines was presented, which allowed for the synthesis of various 2‐aminobenzofuran derivatives in low to moderate yields. This method is applicable to a series of phenyl α‐cyano‐α‐arylacetates with various aryl groups and quinone monoimines with different substituents. In addition, a pausible mechanism was proposed.
A tandem conjugate addition/aromatization/acyl transfer reaction between 3‐aryl‐2‐nitropropanoates and quinone monoimines was described. In the presence of NMM, the reaction proceeded smoothly to give various 1,2‐diarylnitroethanes in low to good yields. The structure of one product was determined by an X‐ray crystal structural analysis. Accordingly, a plausible reaction mechanism was proposed.
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