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The Dimerization of Chiral Allenes: Pairs of Enantiomers and Pairs of Homomers Furnish Different Diastereomers
Author(s) -
Christl Manfred,
Groetsch Stefan,
Günther Kurt
Publication year - 2000
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/1521-3773(20000915)39:18<3261::aid-anie3261>3.0.co;2-t
Subject(s) - diastereomer , enantiomer , methyllithium , selectivity , chemistry , dimer , stereochemistry , organic chemistry , catalysis
Treatment of the pure enantiomer 1 with methyllithium furnishes via cycloallene 2 its dimer 3 with high selectivity. In contrast, racemic 1 yielded only 5 % of 3 and 95 % of the cis isomer of 3 . Thus, racemic 2 is an example of molecular recognition of remarkable selectivity.