A Practical Approach to 6H-Indol-6-ones Enables the Formal Synthesis of γ-Lycorane

Article Chemistry, Organic

Formation of 3-Aminophenols from Cyclohexane-1,3-diones

Damian Szymor-Pietrzak et al.

Summary: meta-Aminophenols are formed by treating 3-amino-2-chlorocyclohex-2-en-1-ones with DBU in MeCN at room temperature, and the chloro compounds are generated by using the halogenating agent BnNMe3·ICl2 in MeOH-CH2Cl2. The amino group must have two substituents, such as two aryl or one aryl and one alkyl group, which can be easily prepared from cyclohex-2-en-1-one and a primary or secondary amine.

JOURNAL OF ORGANIC CHEMISTRY (2021)

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Article Chemistry, Organic

Palladium-Catalyzed Asymmetric Direct Intermolecular Allylation of α-Aryl Cyclic Vinylogous Esters: Divergent Synthesis of (+)-Oxomaritidine and (-)-Mesembrine

Wei Wang et al.

Summary: The study demonstrated that alpha-aryl cyclic vinylogous esters are effective substrates in the direct intermolecular Pd-catalyzed asymmetric allylic alkylation, allowing for the straightforward enantioselective synthesis of common motifs found in various natural products. As an initial application of this protocol, the first catalytic enantioselective total synthesis of (+)-oxomaritidine and an improved five-step catalytic enantioselective synthesis of (-)-mesembrine have been successfully completed in a divergent manner.

ORGANIC LETTERS (2021)

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Article Chemistry, Organic