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N 1 ‐Functionalized Indole‐Phosphane Oxazoline (IndPHOX) Ligands in Asymmetric Allylic Substitution Reactions
Author(s) -
Wang Yu,
Vaismaa Matti J. P.,
Rissanen Kari,
Franzén Robert
Publication year - 2012
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.201101540
Subject(s) - allylic rearrangement , chemistry , oxazoline , amination , substituent , substitution reaction , tsuji–trost reaction , enantioselective synthesis , medicinal chemistry , ligand (biochemistry) , asymmetric induction , kinetic resolution , yield (engineering) , stereochemistry , catalysis , organic chemistry , biochemistry , receptor , materials science , metallurgy
N ‐Functionalized IndPHOX ligands bearing various groups have been synthesized and the effects of the N 1 ‐substituent on the reaction rate, yield, and asymmetric induction in a palladium‐catalyzed allylic substitution reaction are reported. The presence of an oxygen atom in the ligands, namely an N ‐MOM or N ‐THP group, led to enhancement of the enantioselectivity in the allylic amination reaction. In addition, a ligand with a chiral oxazoline ring at C‐1 and a phosphane substituent at C‐2 provided high enantioselectivity in good yield in an asymmetric allylic alkylation reaction.