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Enantioselective Preparation of 2,4‐Disubstituted Azetidines
Author(s) -
Marinetti Angela,
Hubert Philippe,
Genêt JeanPierre
Publication year - 2000
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/(sici)1099-0690(200005)2000:9<1815::aid-ejoc1815>3.0.co;2-8
Subject(s) - chemistry , enantioselective synthesis , palladium , enantiomer , aryl , enantiomeric excess , optically active , phosphorus , medicinal chemistry , organic chemistry , catalysis , combinatorial chemistry , stereochemistry , alkyl
Chiral C 2 ‐symmetric N ‐benzylazetidines have been conveniently prepared from optically pure anti ‐1,3‐diols without loss of enantiomeric purity. N ‐Debenzylation led to the corresponding N ‐unsubstituted azetidines, which were then subjected to palladium‐catalysed coupling reactions with aryl bromides to afford chiral N ‐arylazetidines. ( R , R )‐ N ‐Benzyl‐2,4‐dimethylazetidine has been employed in the synthesis of a new cyclopalladated complex, which can be used, for instance, as a chiral recognition agent for phosphorus ligands.