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High‐Pressure Selectivity Studies—A Simple Route to a Homochiral Wistarin Precursor
Author(s) -
KnappwostGieseke Costanze,
Nerenz Frank,
Wartchow Rudolf,
Winterfeldt Ekkehard
Publication year - 2003
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.200204524
Subject(s) - cyclopentadiene , selectivity , cycloaddition , chemistry , stereochemistry , organic chemistry , catalysis
The cycloaddition of spirobutenolide 3 to the homochiral cyclopentadiene 1 at 6.5 kbar leads exclusively to cycloadduct 5 . Subsequent Diels–Alder or Michael additions again favour the cyclohexenone double bond; this perfect chemo‐ regio‐ and face selectivity was employed for a short and efficient approach to the wistarin framework.
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