Site-Selective and Stereoselective C-H Functionalization of N-Cyclopropylamides via a Directed Remote Metalation Strategy

Yuri Ermolovich, Maryia V. Barysevich, Jasper Adamson, Oksana Rogova, Sandra Kaabel, Ivar Järving, Nicholas Gathergood, Victor Snieckus*, Dzmitry G. Kananovich*

*Corresponding author for this work

Research output: Contribution to journalArticleScientificpeer-review

7 Citations (Scopus)

Abstract

A new methodology for site-selective and stereoselective C-H functionalization of aminocyclopropanes via directed remote lithiation has been developed. Treatment of N-directing group (DG = pivaloyl, tetramethylsuccinimidoyl) arylcyclopropanes with t-BuLi results in a clean β-lithiation and, following quench with electrophiles, leads to a range of cyclopropane derivatives. Sequential double lithiation-methylation to give a dimethylated cyclopropane has been achieved. X-ray, NMR, and computational studies allow rationalization of syn-DG β-deprotonation selectivity via a DG-lithium base coordinated complex.

Original languageEnglish
Pages (from-to)969-973
Number of pages5
JournalOrganic Letters
Volume21
Issue number4
DOIs
Publication statusPublished - 15 Feb 2019
MoE publication typeA1 Journal article-refereed

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