Characterization and utilization of the elusive α,β-unsaturated N-tosyliminium: the synthesis of highly functionalizable skipped halo enynes

Pradhan, Tapas R. ORCID: https://orcid.org/0000-0003-1480-7799, Paudel, Mukti, Harper, Jordan L., Cheong, Paul Ha-Yeon and Park, Jin Kyoon 2021. Characterization and utilization of the elusive α,β-unsaturated N-tosyliminium: the synthesis of highly functionalizable skipped halo enynes. Organic Letters 23 (4) , 1427–1433. 10.1021/acs.orglett.1c00103

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Abstract

A formal haloalkynylation of allenamides has been described for the synthesis of highly stereo- and regioselective skipped halo enynes. Exclusive γ-regioselectivity is achieved through the intermediacy of a conjugated N-tosyliminium intermediate—direct evidence for the formation of which was validated by NMR and HRMS. Quantum mechanical computations reveal that the reactive intermediate geometry is key to controlling the 1,2- or 1,4-regioselectivity of alkyne interception. Divergent access to elusive unsaturated systems has also been reported.

Item Type:	Article
Date Type:	Publication
Status:	Published
Schools:	Schools > Chemistry
Publisher:	American Chemical Society
ISSN:	1523-7060
Date of Acceptance:	4 February 2021
Last Modified:	16 May 2024 01:39
URI:	https://orca.cardiff.ac.uk/id/eprint/165575

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