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Evaluation of Palladacycles as a Non‐Rhodium Based Alternative for the Asymmetric Conjugate 1,4‐Addition of Arylboronic Acids to α,β‐Unsaturated Enones
Author(s) -
Wong Jonathan,
Gan Kennard,
Chen Houguang Jeremy,
Pullarkat Sumod A.
Publication year - 2014
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201400473
Subject(s) - chemistry , conjugate , rhodium , addition reaction , palladium , combinatorial chemistry , transformation (genetics) , organic chemistry , catalysis , mathematical analysis , biochemistry , mathematics , gene
The asymmetric conjugate 1,4‐addition of arylboronic acids to α,β‐unsaturated carbonyl compounds is an extremely versatile and widely used organic transformation. While the rhodium(I)‐catalysed reaction has been thoroughly explored, the asymmetric palladium‐catalysed protocol is far less developed and understood, particularly with acyclic enones as substrates. Herein, we report the systematic evaluation of a series of metallacycles for this reaction and the conjugate addition of arylboronic acids to a wide range of α,β‐unsaturated enones, catalysed by an easily accessible and robust chiral phosphapalladacycle in high yields and enantioselectivities.