Formation of Ketenimines via the Palladium-Catalyzed Decarboxylative π-Allylic Rearrangement of N-Alloc Ynamides

Juliana R. Alexander; Matthew J. Cook

doi:10.1021/acs.orglett.7b02780

Formation of Ketenimines via the Palladium-Catalyzed Decarboxylative π-Allylic Rearrangement of N-Alloc Ynamides

Juliana R. Alexander
, Matthew J. Cook

School of Chemistry and Chemical Engineering

Research output: Contribution to journal › Article › peer-review

16 Citations (Scopus)

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Abstract

A new approach for the formation of ketenimines via a decarboxylative allylic rearrangement pathway that does not require strong stabilizing or protecting groups has been developed. The products can be readily hydrolyzed into their corresponding secondary amides or reacted with sulfur ylides to perform an additional [2,3]-Wittig process. Mechanistic studies suggest an outer-sphere process in which reductive alkylation is rate-limiting.

Original language	English
Pages (from-to)	5822-5825
Number of pages	4
Journal	Organic Letters
Volume	19
Issue number	21
DOIs	https://doi.org/10.1021/acs.orglett.7b02780
Publication status	Published - 20 Oct 2017

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Formation of Ketenimines via the Palladium-Catalyzed Decarboxylative π-Allylic Rearrangement of N-Alloc Ynamides
Copyright © 2017 American Chemical Society. This work is made available online in accordance with the publisher’s policies. Please refer to any applicable terms of use of the publisher.
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Cite this

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title = "Formation of Ketenimines via the Palladium-Catalyzed Decarboxylative π-Allylic Rearrangement of N-Alloc Ynamides",

abstract = "A new approach for the formation of ketenimines via a decarboxylative allylic rearrangement pathway that does not require strong stabilizing or protecting groups has been developed. The products can be readily hydrolyzed into their corresponding secondary amides or reacted with sulfur ylides to perform an additional [2,3]-Wittig process. Mechanistic studies suggest an outer-sphere process in which reductive alkylation is rate-limiting.",

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AB - A new approach for the formation of ketenimines via a decarboxylative allylic rearrangement pathway that does not require strong stabilizing or protecting groups has been developed. The products can be readily hydrolyzed into their corresponding secondary amides or reacted with sulfur ylides to perform an additional [2,3]-Wittig process. Mechanistic studies suggest an outer-sphere process in which reductive alkylation is rate-limiting.

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JO - Organic Letters

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Formation of Ketenimines via the Palladium-Catalyzed Decarboxylative π-Allylic Rearrangement of N-Alloc Ynamides

Abstract

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