Geometry‐Directed Generation and Synthetic Application of α‐Lithio Oxime Ethers

Shimon Shatzmiller*, Rami Lidor, Eytan Shalom, Naim Menashe Eliezer Bahar

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

6 Scopus citations


Several mono‐ and di‐O‐alkyloximes have been regioselectively transformed to the syn α‐lithio derivatives by treatment with n‐butyllithium. The control of oxime ether geometry served to control regioselectivity in α‐lithiation and subsequent carbon‐carbon (alkylation, oxidative coupling) and carbon‐halogen bond formation reactions. The geometry‐directed α‐lithiation‐dimerization sequence was used for the synthesis of large ring compounds.

Original languageEnglish
Pages (from-to)187-194
Number of pages8
JournalIsrael Journal of Chemistry
Issue number2-3
StatePublished - 1989


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