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Face‐Selective and endo ‐Selective Cycloadditions with Enantiomerically Pure Cyclopentadienes
Author(s) -
Beckmann Marion,
Meyer Thorsten,
Schulz Frauke,
Winterfeldt Ekkehard
Publication year - 1994
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.19941271223
Subject(s) - enantiopure drug , chemistry , ketone , bicyclic molecule , enantiomer , selectivity , stereochemistry , organic chemistry , enantioselective synthesis , catalysis
A general synthetic route to the enantiopure bicyclic cyclopentadienes ( S )‐ 3 and ( R )‐ 3 of the hydrindane series, starting from the Hajos‐Wiechert ketone 4 or its enantiomer is described. Reasons for the excellent face and endo selectivity of cycloadditions and the resulting consequences for chiral recognition are discussed.