Sparteine-Free, Highly Stereoselective Construction of Complex Allylic Alcohols Using 1,2-Metallate Rearrangements.
Journal
JACS Au
ISSN: 2691-3704
Titre abrégé: JACS Au
Pays: United States
ID NLM: 101775714
Informations de publication
Date de publication:
26 Jun 2023
26 Jun 2023
Historique:
received:
08
03
2023
revised:
02
05
2023
accepted:
03
05
2023
medline:
30
6
2023
pubmed:
30
6
2023
entrez:
30
6
2023
Statut:
epublish
Résumé
Stereotriads bearing allylic alcohols are privileged structures in natural products, and new methods accessing these in a stereoselective fashion are highly sought after. Toward this goal, we found that the use of chiral polyketide fragments allows for performing the Hoppe-Matteson-Aggarwal rearrangement in the absence of sparteine with high yields and diastereoselectivities, rendering this protocol a highly valuable alternative to the Nozaki-Hiyama-Takai-Kishi reaction. The switch of directing groups in most cases resulted in the reversed stereochemical outcome, which could be explained by conformational analysis on density functional theory level and a Felkin-like model.
Identifiants
pubmed: 37388702
doi: 10.1021/jacsau.3c00114
pmc: PMC10301690
doi:
Types de publication
Journal Article
Langues
eng
Pagination
1695-1710Informations de copyright
© 2023 The Authors. Published by American Chemical Society.
Déclaration de conflit d'intérêts
The authors declare no competing financial interest.
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