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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. 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.


Item Type:Article
Related URLs:
URLURL TypeDescription
https://doi.org/10.1016/j.tetlet.2017.07.022DOIArticle
http://www.sciencedirect.com/science/article/pii/S0040403917308559PublisherArticle
https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5578629/PubMed CentralArticle
https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5578629/#PubMed CentralSupplementary Materials
ORCID:
AuthorORCID
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.
Funders:
Funding AgencyGrant Number
NIHR01GM080269
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: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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