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Switching Selectivity in o ‐Benzoquinone Cycloadditions
Author(s) -
AlTalib Mahmoud,
Gerstenberger Ina,
Jones Peter G.,
Winterfeldt Ekkehard
Publication year - 1997
Publication title -
liebigs annalen
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 0947-3440
DOI - 10.1002/jlac.199719970517
Subject(s) - chemistry , regioselectivity , cyclopentadiene , chemoselectivity , selectivity , adduct , benzoquinone , derivative (finance) , cycloaddition , medicinal chemistry , 1,4 benzoquinone , organic chemistry , quinone , catalysis , financial economics , economics
Whereas m ‐methoxy‐ o ‐benzoquinone 6 , like other unsaturated ketones, operates as a dienophile in Diels–Alder cycloadditions, the corresponding methyl derivative 7a behaves as an electron‐poor 4π‐system under exactly the same conditions. With the nonsymmetric cyclopentadiene 2 (X = MeO), adduct 9a is formed with excellent chemoselectivity, face‐selectivity, and regioselectivity.