Accessing Spiropiperidines from Dihydropyridones through Tandem Triflation-Allylation and Ring-Closing Metathesis (RCM) - Archive ouverte HAL Access content directly
Journal Articles Organic & Biomolecular Chemistry Year : 2023

Accessing Spiropiperidines from Dihydropyridones through Tandem Triflation-Allylation and Ring-Closing Metathesis (RCM)

Abstract

A novel approach to build 2-spiropiperidine moieties starting from dihydropyridones was developed. The triflic anhydridepromoted conjugate addition of allyltributylstannane onto these dihydropyridones allowed for the formation of gem bisalkenyl intermediates that were converted to the corresponding spirocarbocycles with excellent yields via ring closing metathesis. The vinyl triflate group generated onto these 2-spiro-dihydropyridine intermediates could be successfuly used as a chemical expansion vector for further transformations namelly Pd-catalyzed cross-coupling reactions.
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Dates and versions

hal-04159035 , version 1 (11-07-2023)

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Naresh Gantasala, Corentin Fournet, Myriam Le Roch, Claudia Lalli, Srihari Pabbaraja, et al.. Accessing Spiropiperidines from Dihydropyridones through Tandem Triflation-Allylation and Ring-Closing Metathesis (RCM). Organic & Biomolecular Chemistry, 2023, 21 (25), pp.5245-5253. ⟨10.1039/D3OB00545C⟩. ⟨hal-04159035⟩
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