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Enantioselective Iridium-Catalyzed Allylic Alkylation Reactions of Masked Acyl Cyanide Equivalents

Hethcox, J. Caleb and Shockley, Samantha E. and Stoltz, Brian M. (2017) Enantioselective Iridium-Catalyzed Allylic Alkylation Reactions of Masked Acyl Cyanide Equivalents. Organic Letters, 19 (7). pp. 1527-1529. ISSN 1523-7060. PMCID PMC5470644. https://resolver.caltech.edu/CaltechAUTHORS:20170316-160746005

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Abstract

The first enantioselective iridium-catalyzed allylic alkylation reaction of a masked acyl cyanide (MAC) reagent has been developed. The transformation allows for the use of an umpoled synthon, which serves as a carbon monoxide equivalent. The reaction proceeds with good yield and excellent selectivity up to gram scale for a wide range of substituted allylic electrophiles, delivering products amenable to the synthesis of highly desirable, enantioenriched vinylated α-aryl carbonyl derivatives.


Item Type:Article
Related URLs:
URLURL TypeDescription
https://dx.doi.org/10.1021/acs.orglett.7b00449DOIArticle
http://pubs.acs.org/doi/abs/10.1021/acs.orglett.7b00449PublisherArticle
http://pubs.acs.org/doi/suppl/10.1021/acs.orglett.7b00449PublisherSupporting Information
https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5470644PubMed CentralArticle
ORCID:
AuthorORCID
Stoltz, Brian M.0000-0001-9837-1528
Additional Information:© 2017 American Chemical Society. Received 14 February 2017. Published online 14 March 2017. The NIH-NIGMS (R01GM080269) and Caltech are thanked for support of our research program. Additionally, J.C.H. thanks the Camille and Henry Dreyfus postdoctoral program in Environmental Chemistry, and S.E.S. thanks the NIH-NIGMS for a predoctoral fellowship (F31GM120804). Dr. Mona Shahgholi (Caltech) and Naseem Torian (Caltech) are thanked for mass spectrometry assistance. Dr. Scott Virgil (Caltech) is thanked for assistance with instrumentation. J.C.H. and S.E.S. contributed equally. The authors declare no competing financial interest.
Funders:
Funding AgencyGrant Number
NIHR01GM080269
CaltechUNSPECIFIED
Camille and Henry Dreyfus FoundationUNSPECIFIED
NIH Predoctoral FellowshipF31GM120804
Issue or Number:7
PubMed Central ID:PMC5470644
Record Number:CaltechAUTHORS:20170316-160746005
Persistent URL:https://resolver.caltech.edu/CaltechAUTHORS:20170316-160746005
Official Citation:Enantioselective Iridium-Catalyzed Allylic Alkylation Reactions of Masked Acyl Cyanide Equivalents J. Caleb Hethcox, Samantha E. Shockley, and Brian M. Stoltz Organic Letters 2017 19 (7), 1527-1529 DOI: 10.1021/acs.orglett.7b00449
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:75189
Collection:CaltechAUTHORS
Deposited By: George Porter
Deposited On:16 Mar 2017 23:22
Last Modified:03 Oct 2019 16:47

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