N 1 ‐Functionalized Indole‐Phosphane Oxazoline (IndPHOX) Ligands in Asymmetric Allylic Substitution Reactions

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...

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Bibliographic Details
Published in:European journal of organic chemistry 2012-03, Vol.2012 (8), p.1569-1576
Main Authors: Wang, Yu, Vaismaa, Matti J. P., Rissanen, Kari, Franzén, Robert
Format: Article
Language:English
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Summary: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.
ISSN:1434-193X
1099-0690
DOI:10.1002/ejoc.201101540