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Development and application of a palladium-​catalyzed enantioselective conjugate addition

Holder, Jeffrey C. and Shockley, Samantha E. and Marziale, Alexander N. and Gatti, Michele and Kikushima, Kotaro and Stoltz, Brian M. (2014) Development and application of a palladium-​catalyzed enantioselective conjugate addition. In: 248th American Chemical Society National Meeting & Exposition, August 10-14, 2014, San Francisco, CA.

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The first enantioselective palladium-catalyzed, asym. construction of all-carbon quaternary stereocenters via 1, 4-addn. of arylboronic acids to cyclic, β-substituted enones is reported. A wide range of arylboronic acids and cyclic enones are reacted utilizing a catalyst prepd. from palladium(II) trifluoroacetate and a chiral pyridinooxazoline ligand to yield enantioenriched products bearing benzylic stereocenters. Recently, this methodol. has been expanded to support the reaction of heterocyclic chromone and 4-quinolone conjugate acceptors. Notably, this transformation is insensitive to air or moisture, providing a practical and operationally simple method of synthesizing enantioenriched stereocenters. The application of this reaction toward the total syntheses of members of the taiwaniaquinone sesquiterpenoid family of natural products is discussed.

Item Type:Conference or Workshop Item (Paper)
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Stoltz, Brian M.0000-0001-9837-1528
Additional Information:© 2014 American Chemical Society.
Record Number:CaltechAUTHORS:20140811-150326033
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Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:48343
Deposited By: Tony Diaz
Deposited On:11 Aug 2014 22:06
Last Modified:03 Oct 2019 07:02

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