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Direct Synthesis of Polycyclic Tropinones by a Condensation–[4+3]‐Cycloaddition Cascade Reaction
Author(s) -
Okamoto Tsubasa,
Shibata Miki,
Karanjit Sangita,
Nakayama Atsushi,
Yoshida Masahiro,
Namba Kosuke
Publication year - 2018
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201802011
Subject(s) - cycloaddition , chemistry , intramolecular force , aldehyde , pyrrole , diastereomer , cascade reaction , condensation reaction , acrolein , nucleophile , nucleophilic addition , organic chemistry , combinatorial chemistry , catalysis
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.