Abstract
Spirocyclic butyrolactones and butenolides are widespread structural motifs in bioactive substances. Despite their prevalence, a simple method ensuring their direct preparation from exocyclic alkenes, ideally in a late-stage context, remains elusive. Herein, we report direct aminolactone formation using unactivated alkenes which addresses this gap, employing cheap and readily available reactants. The method relies on the hijacking of a cationic aminoalkylation pathway and affords (spiro)aminolactones with excellent functional group tolerance and chemoselectivity. The synthetic versatility of the products is demonstrated through a range of transformations, notably exploiting stereospecific rearrangement chemistry to produce sterically congested scaffolds.
Original language | English |
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Pages (from-to) | 10806-10811 |
Number of pages | 6 |
Journal | Chemical Science |
Volume | 14 |
Issue number | 39 |
DOIs | |
Publication status | Published - 28 Sep 2023 |
Austrian Fields of Science 2012
- 104015 Organic chemistry