Shockley, Samantha E. and Hethcox, J. Caleb and Stoltz, Brian M. (2017) Enantioselective Synthesis of Acyclic α-Quaternary Carboxylic Acid Derivatives through Iridium-Catalyzed Allylic Alkylation. Angewandte Chemie International Edition, 56 (38). pp. 11545-11548. ISSN 1433-7851. https://resolver.caltech.edu/CaltechAUTHORS:20170719-091950600
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Abstract
The first highly enantioselective iridium-catalyzed allylic alkylation providing access to products bearing an allylic all-carbon quaternary stereogenic center has been developed. The reaction utilizes a masked acyl cyanide (MAC) reagent, which enables the one-pot preparation of α-quaternary carboxylic acids, esters, and amides with a high degree of enantioselectivity. The utility of these products is further explored via a series of diverse product transformations.
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| Alternate Title: | Enantioselective Synthesis of Acyclic α-Quaternary Carboxylic Acid Derivatives via Iridium-Catalyzed Allylic Alkylation | ||||||||||
| Additional Information: | © 2017 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim. Manuscript received: July 10, 2017; Accepted manuscript online: July 19, 2017; Version of record online: August 9, 2017. The NIH-NIGMS (R01GM080269) and Caltech are thanked for support of our research program. J.C.H. thanks the Camille and Henry Dreyfus postdoctoral program, and S.E.S. thanks the NIH-NIGMS for a predoctoral fellowship (F31GM120804). Dr. Michael Takase, Dr. Lawrence Henling, and Niklas Thompson are acknowledged for assistance with X-ray analysis. Dr. Mona Shahgholi and Naseem Torian are thanked for mass spectrometry assistance. Dr. Scott Virgil is thanked for assistance with instrumentation. The authors declare no conflict of interest. | ||||||||||
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| Subject Keywords: | allylic alkylation; carboxylic acid derivatives; iridium; quaternary stereocenter; umpolung | ||||||||||
| Issue or Number: | 38 | ||||||||||
| Record Number: | CaltechAUTHORS:20170719-091950600 | ||||||||||
| Persistent URL: | https://resolver.caltech.edu/CaltechAUTHORS:20170719-091950600 | ||||||||||
| Official Citation: | S. E. Shockley, J. C. Hethcox, B. M. Stoltz, Angew. Chem. Int. Ed. 2017, 56, 11545 | ||||||||||
| Usage Policy: | No commercial reproduction, distribution, display or performance rights in this work are provided. | ||||||||||
| ID Code: | 79196 | ||||||||||
| Collection: | CaltechAUTHORS | ||||||||||
| Deposited By: | Tony Diaz | ||||||||||
| Deposited On: | 19 Jul 2017 16:29 | ||||||||||
| Last Modified: | 03 Oct 2019 18:17 |
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