Kikushima, Kotaro and Holder, Jeffrey C. and Gatti, Michele and Stoltz, Brian M. (2011) Palladium-Catalyzed Asymmetric Conjugate Addition of Arylboronic Acids to Five-, Six-, and Seven-Membered β-Substituted Cyclic Enones: Enantioselective Construction of All-Carbon Quaternary Stereocenters. Journal of the American Chemical Society, 133 (18). pp. 6902-6905. ISSN 0002-7863 http://resolver.caltech.edu/CaltechAUTHORS:20110608-104503600
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Abstract
The first enantioselective Pd-catalyzed construction of all-carbon quaternary stereocenters via 1,4-addition of arylboronic acids to β-substituted cyclic enones is reported. Reaction of a wide range of arylboronic acids and cyclic enones using a catalyst prepared 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.
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| Additional Information: | © 2011 American Chemical Society. Received: January 23, 2011. Published: April 15, 2011. This publication is based on work supported by Award No. KUS-11-006-02, made by King Abdullah University of Science and Technology (KAUST). The authors wish to thank NIH-NIGMS (R01GM080269-01), Amgen, Abbott, Boehringer Ingelheim, and Caltech for financial support. K.K. acknowledges the Japan Society for the Promotion of Science for a postdoctoral fellowship. M.G. is grateful to the Swiss National Science Foundation for financial support through a postdoctoral fellowship. | ||||||||||||||||||
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| Record Number: | CaltechAUTHORS:20110608-104503600 | ||||||||||||||||||
| Persistent URL: | http://resolver.caltech.edu/CaltechAUTHORS:20110608-104503600 | ||||||||||||||||||
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| Official Citation: | Palladium-Catalyzed Asymmetric Conjugate Addition of Arylboronic Acids to Five-, Six-, and Seven-Membered β-Substituted Cyclic Enones: Enantioselective Construction of All-Carbon Quaternary Stereocenters Kotaro Kikushima, Jeffrey C. Holder, Michele Gatti, Brian M. Stoltz Journal of the American Chemical Society 2011 133 (18), 6902-6905 | ||||||||||||||||||
| Usage Policy: | No commercial reproduction, distribution, display or performance rights in this work are provided. | ||||||||||||||||||
| ID Code: | 23941 | ||||||||||||||||||
| Collection: | CaltechAUTHORS | ||||||||||||||||||
| Deposited By: | Tony Diaz | ||||||||||||||||||
| Deposited On: | 16 Jun 2011 21:44 | ||||||||||||||||||
| Last Modified: | 26 Dec 2012 13:18 |
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