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An easy access to ( S )‐ and ( R )‐hydroxycyclohexenone
Author(s) -
Brünjes Rainer,
Tilstam Ulf,
Winterfeldt Ekkehard
Publication year - 1991
Publication title -
chemische berichte
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.667
H-Index - 136
eISSN - 1099-0682
pISSN - 0009-2940
DOI - 10.1002/cber.19911240732
Subject(s) - chemistry , cyclopentadiene , regioselectivity , ketone , adduct , stereoselectivity , quinone , enone , diels–alder reaction , medicinal chemistry , stereochemistry , organic chemistry , catalysis
The Diels‐Alder adduct obtained by addition of quinone to the chiral cyclopentadiene 2 undergoes regioselective and stereoselective reduction after hydrogenation. The 4‐hydroxy ketone 3 thus formed yields the title compound 1 in a thermal retro Diels‐Alder process.