Geometry-Directed Generation and Synthetic Application of α-Lithio Oxime Ethers |
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| Authors: | Shimon Shatzmiller Rami Lidor Eytan Shalom Naim Menashe Eliezer Bahar |
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| Affiliation: | School of Chemistry, Raymond and Beverly Sackler Faculty of Exact Sciences, Tel Aviv University, Tel Aviv 69978, Israel |
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| Abstract: | 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. |
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