Pradhan, Tapas R. ![]() |
Official URL: https://doi.org/10.1021/acs.orglett.1c00103
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 |
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Date Type: | Publication |
Status: | Published |
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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