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.
Original language | English |
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Pages (from-to) | 581-585 |
Number of pages | 5 |
Journal | Synlett |
Volume | 30 |
Issue number | 5 |
DOIs | |
Publication status | Published - 2019 |
Keywords
- allyl silanes
- cycloaddition
- heterocycles
- isocyanates
- lactams
- palladium
- Tsuji-Trost allylation
ASJC Scopus subject areas
- Organic Chemistry
Fields of Expertise
- Human- & Biotechnology