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- Title
Direct Synthesis of Polycyclic Tropinones by a Condensation–[4+3]‐Cycloaddition Cascade Reaction.
- Authors
Okamoto, Tsubasa; Shibata, Miki; Karanjit, Sangita; Nakayama, Atsushi; Yoshida, Masahiro; Namba, Kosuke
- Abstract
Abstract: A concise method of constructing polycyclic tropinone frameworks was developed. The single‐step synthesis of polycyclic tropinone consists of an intramolecular [4+3] cycloaddition reaction of N‐nosyl‐pyrrole with oxyallyl cation that was generated in situ by an intermolecular condensation reaction of the nucleophilic functional groups on a tethered pyrrole with the aldehyde of 2‐(silyloxy)‐acrolein. This cascade reaction afforded various polycyclic tropinones including tri‐, tetra‐, and pentacyclic systems in high yields as single diastereomers.
- Subjects
CHEMICAL synthesis; TROPINONES; CONDENSATION reactions; RING formation (Chemistry); CHEMICAL reactions; STEREOSELECTIVE reactions; CARBONYL compounds; DIASTEREOISOMERS
- Publication
Chemistry - A European Journal, 2018, Vol 24, Issue 38, p9508
- ISSN
0947-6539
- Publication type
Article
- DOI
10.1002/chem.201802011