Holder, Jeffrey C. and Kikushima, Kotaro and Marziale, Alexander N. and Gatti, Michele and Stoltz, Brian M. (2013) Development of a palladium-catalyzed enantioselective conjugate addition of arylboronic acids to cyclic conjugate acceptors. In: 245th ACS National Meeting & Exposition, Abstracts of Papers, April 7-11, 2013, New Orleans, LA. https://resolver.caltech.edu/CaltechAUTHORS:20130410-144615697
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Abstract
The first enantioselective Pd-catalyzed construction of all-carbon quaternary stereocenters via 1,4-addn. of arylboronic acids to β-substituted cyclic enones is reported. Reaction of a wide range of arylboronic acids and cyclic enones using a catalyst prepd. from Pd(OCOCF_3)_2 and a chiral pyridinooxazoline ligand yields enantioenriched products bearing benzylic stereocenters. Notably, this transformation is tolerant to air and moisture, providing a practical and operationally simple method of synthesizing enantioenriched all-carbon quaternary stereocenters.
| Item Type: | Conference or Workshop Item (Paper) | ||||||
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| Additional Information: | © 2013 American Chemical Society. | ||||||
| Record Number: | CaltechAUTHORS:20130410-144615697 | ||||||
| Persistent URL: | https://resolver.caltech.edu/CaltechAUTHORS:20130410-144615697 | ||||||
| Usage Policy: | No commercial reproduction, distribution, display or performance rights in this work are provided. | ||||||
| ID Code: | 37870 | ||||||
| Collection: | CaltechAUTHORS | ||||||
| Deposited By: | Tony Diaz | ||||||
| Deposited On: | 12 Aug 2013 22:38 | ||||||
| Last Modified: | 03 Oct 2019 04:51 |
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