[2,3]-Wittig Rearrangement as a Formal Asymmetric Alkylation of α-Branched Ketones

Mariliis Kimm, Maksim Ošeka, Sandra Kaabel, Andrus Metsala, Ivar Järving, Tõnis Kanger*

*Corresponding author for this work

Research output: Contribution to journalArticleScientificpeer-review

6 Citations (Scopus)

Abstract

The enantioselective [2,3]-Wittig rearrangement of cinnamyloxycyclopentanone derivatives was performed in the presence of a Cinchona-based primary amine. The described method provides synthetically valuable α-hydroxy ketones with quaternary stereogenic centers in excellent enantiomeric purities. Relying on the X-ray crystal structure of the product and the DFT calculations, we propose that the rearrangement is promoted by an intramolecular hydrogen bond between the substrate and the catalyst.

Original languageEnglish
Pages (from-to)4976-4980
Number of pages5
JournalOrganic Letters
Volume21
Issue number13
DOIs
Publication statusPublished - 5 Jul 2019
MoE publication typeA1 Journal article-refereed

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