The Carbene Chemistry of N-Sulfonyl Hydrazones: The Past, Present, and Future

Chemical Reviews, Год журнала: 2025, Номер unknown

Опубликована: Янв. 10, 2025

N-Sulfonyl hydrazones have been extensively used as operationally safe carbene precursors in modern organic synthesis due to their ready availability, facile functionalization, and environmental benignity. Over the past two decades, there has tremendous progress chemistry of N-sulfonyl presence transition metal catalysts, under metal-free conditions, or using photocatalysts photoirradiation conditions. Many transfer reactions are unique cannot be achieved by any alternative methods. The discovery novel development highly enantioselective new skeletal editing represent notable recent achievements hydrazones. This review describes overall made hydrazones, organized based on reaction types, spotlighting current state-of-the-art remaining challenges addressed future. Special emphasis is devoted identifying, describing, comparing scope limitations methodologies, key mechanistic scenarios, potential applications complex molecules.

Язык: Английский

Catalytic Asymmetric Approach to the Naturally Occurring Clavine Alkaloid, (+)-Lysergine

Synthesis, Год журнала: 2024, Номер unknown

Опубликована: Авг. 13, 2024

Abstract An efficient asymmetric approach to the ergot alkaloids has been achieved via a highly regioselective Heck cyclization. Asymmetric induction of key intermediate was catalytic enantioselective α-aminoxylation catalyzed by d-proline (98% ee). Utilizing aforementioned strategy, formal total synthesis (+)-lysergine and (+)-isolysergine achieved. Importantly, an unnatural analogues (–)-lysergine (–)-isolysergine also using l-proline.

Язык: Английский