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Dianionic Oxy‐Cope Rearrangement with Benzil Derivatives: meso ‐Selective 3,3‐Coupling of Two Tetrahydrofuran Moieties
Author(s) -
Abdelhamid Ismail Abdelshafy,
Abdelmoniem Amr Mohamed,
Fohrer Jörg,
Bardenhorst Iris,
Wartchow Rudolf,
Butenschön Holger
Publication year - 2017
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201701397
Subject(s) - chemistry , benzil , diastereomer , aldol reaction , intramolecular force , adduct , tetrahydrofuran , stereochemistry , cope rearrangement , cyclobutanes , catalysis , organic chemistry , cycloaddition , solvent
Benzil and its derivatives naphthil and pyridil have been found to undergo a dianionic oxy‐Cope rearrangement upon reaction with 2‐lithio‐4,5‐dihydrofuran to give 3,3′‐octahydrobifuranyls selectively as the meso diastereomers. The diastereoselectivity is explained based on the reaction mechanism and the conformation of the starting material. 4,4′‐Di‐ tert ‐butylbenzil gave the respective intramolecular aldol adduct, whose relative configuration was determined by NOE experiments.