Accessing spiropiperidines from dihydropyridones through tandem triflation-allylation and ring-closing metathesis (RCM)

A novel approach to build 2-spiropiperidine moieties starting from dihydropyridones was developed. The triflic anhydride-promoted conjugate addition of allyltributylstannane onto dihydropyridones allowed for the formation of gem bis-alkenyl intermediates that were converted to the corresponding spir...

Full description

Saved in:
Bibliographic Details
Published in:Organic & biomolecular chemistry 2023-06, Vol.21 (25), p.5245-5253
Main Authors: Gantasala, Naresh, Fournet, Corentin, Le Roch, Myriam, Lalli, Claudia, Pabbaraja, Srihari, Gouault, Nicolas
Format: Article
Language:English
Subjects:
Allyl compounds
Chemical reactions
Chemical Sciences
Cross coupling
Dihydropyridine
Intermediates
Metathesis
Organic chemistry
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:A novel approach to build 2-spiropiperidine moieties starting from dihydropyridones was developed. The triflic anhydride-promoted conjugate addition of allyltributylstannane onto dihydropyridones allowed for the formation of gem bis-alkenyl intermediates that were converted to the corresponding spirocarbocycles with excellent yields via ring closing metathesis. The vinyl triflate group generated on these 2-spiro-dihydropyridine intermediates could be successfully used as a chemical expansion vector for further transformations namely Pd-catalyzed cross-coupling reactions. We report an approach to build 2-spiropiperidine moieties starting from dihydropyridones through a tandem triflation-allylation reaction followed by ring-closing metathesis and then Pd-catalyzed functionalization.
ISSN:1477-0520
1477-0539
DOI:10.1039/d3ob00545c