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Asymmetric Synthesis of All-Carbon Quaternary Spirocycles via a Catalytic Enantioselective Allylic Alkylation Strategy

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. doi:10.1016/j.tetlet.2017.07.022.

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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.

Item Type:Article
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URLURL TypeDescription CentralArticle
Shockley, Samantha E.0000-0001-5682-8569
Hethcox, J. Caleb0000-0002-7712-308X
Stoltz, Brian M.0000-0001-9837-1528
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.
Funding AgencyGrant Number
Camille and Henry Dreyfus FoundationUNSPECIFIED
NIH Predoctoral FellowshipF31GM120804
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:
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,
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:78843
Deposited On:07 Jul 2017 17:13
Last Modified:24 Mar 2022 23:15

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