Abstract
Pd/DPEphos catalyzes the [3+2] cycloaddition of various alkyl isocyanates with 2-acetoxymethyl-3-allyltrimethylsilane as a synthetic equivalent of trimethylenemethane (TMM). Taking advantage of 2-acetoxymethyl-3-allyltrimethylsilane acting both as nucleophile as well as electrophile this reaction gives a convenient access to 5-ring lactams with an exocyclic alkene moiety. The formation of the β,γ-unsaturated 2-pyrrolidinones occurs without olefin isomerization and without epimerization of the stereogenic centers. Mechanistic investigations suggest an initial N-allylation of the isocyanate followed by nucleophilic ring closure furnishing the desired 2-pyrrolidinones.
Originalsprache | englisch |
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Seiten (von - bis) | 581-585 |
Seitenumfang | 5 |
Fachzeitschrift | Synlett |
Jahrgang | 30 |
Ausgabenummer | 5 |
DOIs | |
Publikationsstatus | Veröffentlicht - 2019 |
ASJC Scopus subject areas
- Organische Chemie
Fields of Expertise
- Human- & Biotechnology