Shockley, Samantha E. and Hethcox, J. Caleb and Stoltz, Brian M. (2017) Asymmetric Synthesis of All-Carbon Quaternary Spirocycles via a Catalytic Enantioselective Allylic Alkylation Strategy. Tetrahedron Letters, 58 (34). pp. 3341-3343. ISSN 0040-4039. PMCID PMC5578629. https://resolver.caltech.edu/CaltechAUTHORS:20170707-100417876
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Abstract
Rapid access to enantioenriched spirocycles possessing a 1,4-dicarbonyl moiety spanning an all-carbon quaternary stereogenic spirocenter was achieved using a masked bromomethyl vinyl ketone reagent. The developed protocol entails an enantioselective palladium-catalyzed allylic alkylation reaction followed by a one-pot unmasking/RCM sequence that provides access to the spirocyclic compounds in good yields and selectivities.
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| Additional Information: | © 2017 Elsevier Ltd. Received 27 June 2017, Accepted 3 July 2017, Available online 5 July 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. Mona Shahgholi and Naseem Torian (Caltech) are thanked for mass spectrometry assistance. Dr. Scott Virgil (Caltech) is thanked for assistance with instrumentation. | |||||||||||||||
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| Subject Keywords: | Allylic alkylation; Spirocycle; Asymmetric catalysis; Palladium catalysis; Masked bromomethyl vinyl ketone | |||||||||||||||
| Issue or Number: | 34 | |||||||||||||||
| PubMed Central ID: | PMC5578629 | |||||||||||||||
| Record Number: | CaltechAUTHORS:20170707-100417876 | |||||||||||||||
| Persistent URL: | https://resolver.caltech.edu/CaltechAUTHORS:20170707-100417876 | |||||||||||||||
| Official Citation: | Samantha E. Shockley, J. Caleb Hethcox, Brian M. Stoltz, Asymmetric synthesis of all-carbon quaternary spirocycles via a catalytic enantioselective allylic alkylation strategy, Tetrahedron Letters, Volume 58, Issue 34, 2017, Pages 3341-3343, ISSN 0040-4039, http://dx.doi.org/10.1016/j.tetlet.2017.07.022. (http://www.sciencedirect.com/science/article/pii/S0040403917308559) | |||||||||||||||
| Usage Policy: | No commercial reproduction, distribution, display or performance rights in this work are provided. | |||||||||||||||
| ID Code: | 78843 | |||||||||||||||
| Collection: | CaltechAUTHORS | |||||||||||||||
| Deposited By: | Ruth Sustaita | |||||||||||||||
| Deposited On: | 07 Jul 2017 17:13 | |||||||||||||||
| Last Modified: | 03 Oct 2019 18:12 |
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