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Erratum: Development of a generic activation mode: nucleophilic a-substitution of ketones via oxy-allyl cations

Author(s): Dilger, Andrew K.; MacMillan, David W.C.; Vander Wal, Mark N.

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Abstract: Oxy-allyl cations have been known as transient electrophilic species since they were first proposed as intermediates in the Favorskii rearrangement in 1894. Since that time, they also have been used as a mode of activation for [4 + 3] cycloadditions in a variety of natural product syntheses. In this manuscript, we describe a method for the interception of oxy-allyl cations with a diverse range of common nucleophiles, thereby demonstrating the value of this intermediate as a generic mode of activation. This simple, mild, room temperature protocol allows for the formation of a variety of high value carbon–carbon and carbon–heteroatom bonds that are readily incorporated within a series of cyclic and acyclic ketone systems. Initial efforts into the development of an enantioselective catalytic variant are also described.
Publication Date: 1-Dec-2013
Citation: Vander Wal, M. N., Dilger, A. K., & MacMillan, D. W. C. (2013). Erratum: Development of a generic activation mode: Nucleophilic a-substitution of ketones via oxy-allyl cations (Chemical Science (2013) 4 (3075-3079) DOI: 10.1039/c3sc51266e). Chemical Science, 4(12).
DOI: doi:10.1039/c3sc90044d
ISSN: 2041-6520
EISSN: 2041-6539
Pages: 4, 3075 - 3079
Type of Material: Journal Article
Journal/Proceeding Title: Chemical Science
Version: Final published version. Article is made available in OAR by the publisher's permission or policy.
Notes: Erratum.

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