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Abstract Intramolecular pyridinium oxide cycloadditions form complex polycyclic nitrogenous architectures. The diastereoselectivity and regioselectivity of pyridinium oxide cycloadditions was systematically investigated for the first time using complex substrates. Predictably high levels of diastereoselectivity and regioselectivity are observed, which can be attributed to minimization of steric (syn‐pentane) and torsional strain in the products. The reaction is reversible under the reaction conditions, and it is stereospecific with respect to the dipolarophile geometry.
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Abstract A Diels–Alder reaction‐based strategy for the synthesis of indoles and related heterocycles is reported. An intramolecular cycloaddition of alkyne‐tethered 3‐aminopyrones gives 4‐substituted indolines in good yield and with complete regioselectivity. Additional substitution is readily tolerated in the transformation, allowing synthesis of complex and non‐canonical substitution patterns. Oxidative conditions give the corresponding indoles. The strategy also allows the synthesis of carbazoles. The method was showcased in a formal synthesis of lysergic acid.more » « less
