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4,8‐Disubstituted Bicyclo[3.3.1]nona‐2,6‐dienes as Chiral Ligands for Rh‐Catalyzed Asymmetric 1,4‐Addition Reactions
Author(s) -
Rimkus Renaldas,
Jurgelėnas Marius,
Stončius Sigitas
Publication year - 2015
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/ejoc.201500202
Subject(s) - chemistry , bicyclic molecule , conjugate , nonane , diene , catalysis , rhodium , enantioselective synthesis , medicinal chemistry , stereochemistry , bridged compounds , organic chemistry , mathematical analysis , natural rubber , mathematics
C 2 ‐symmetric chiral diene ligands based on 4,8‐ endo , endo ‐disubstituted bicyclo[3.3.1]nona‐2,6‐diene framework have been designed and synthesized. The rhodium complexes of the dienes, which were obtained in a few straightforward steps from enantiomerically pure bicyclo[3.3.1]nonane‐2,6‐dione, exhibited excellent catalytic activity and high enantioselectivity (up to 96 % ee ) in the conjugate addition reaction of arylboronic acids to cyclic enones under mild reaction conditions with high atom efficiency.