Highly Regioselective Addition of Allylic Zinc Halides and Various Zinc Enolates to [1.1.1]Propellane.
[1.1.1]propellane
allylic zinc halides
strained molecules
zinc enolates
Journal
Angewandte Chemie (International ed. in English)
ISSN: 1521-3773
Titre abrégé: Angew Chem Int Ed Engl
Pays: Germany
ID NLM: 0370543
Informations de publication
Date de publication:
02 Nov 2020
02 Nov 2020
Historique:
received:
07
07
2020
pubmed:
4
8
2020
medline:
4
8
2020
entrez:
4
8
2020
Statut:
ppublish
Résumé
We report a range of highly regioselective openings of [1.1.1]propellane with various allylic zinc halides, as well as zinc enolates of ketones, esters and nitriles. The resulting zincated bicyclopentanes (BCPs) were trapped with a range of electrophiles including acyl chlorides, sulfonothioates, hydroxylamino benzoates, tosyl cyanide as well as aryl and allyl halides, generating highly functionalized BCP-derivatives. The unusually high regioselectivity of these reactions has been rationalized using DFT calculations. A bioisostere of the synthetic opioid pethidine was prepared in 95 % yield in one step using this method.
Identifiants
pubmed: 32744419
doi: 10.1002/anie.202009340
pmc: PMC7693202
doi:
Types de publication
Journal Article
Langues
eng
Sous-ensembles de citation
IM
Pagination
20235-20241Informations de copyright
© 2020 The Authors. Published by Wiley-VCH GmbH.
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