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. https://resolver.caltech.edu/CaltechAUTHORS:20140811-150326033
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Abstract
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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| Additional Information: | © 2014 American Chemical Society. | ||||||
| Record Number: | CaltechAUTHORS:20140811-150326033 | ||||||
| Persistent URL: | https://resolver.caltech.edu/CaltechAUTHORS:20140811-150326033 | ||||||
| Usage Policy: | No commercial reproduction, distribution, display or performance rights in this work are provided. | ||||||
| ID Code: | 48343 | ||||||
| Collection: | CaltechAUTHORS | ||||||
| Deposited By: | Tony Diaz | ||||||
| Deposited On: | 11 Aug 2014 22:06 | ||||||
| Last Modified: | 03 Oct 2019 07:02 |
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