Toward a Better Understanding on the Mechanism of Ortholithiation. Tuning of Selectivities in the Metalation of meta-Anisic Acid by an Appropriate Choice of Base

• DOI: 10.1021/ol050761c
• Publication Date: 2005-06-02T04:48:28Z
• Authors: Thi-Huu Nguyen; Nguyet Trang Than...; Anne-Sophie Castanet; Kim Phi Phung Nguyen; Jacques Mortier
• Keywords: Metalation; Heteroatom; Base (topology); Surface Modification; Position (finance)

If employed in THF at 0 °C, LTMP metalates meta-anisic acid the doubly activated position. In contrast, n-BuLi/t-BuOK deprotonates position C-4 preferentially low temperature. Functionalization C-6 requires protection of C-2 site beforehand. As a result these findings, new mechanism is proposed for heteroatom-directed ortholithiation aromatic compounds.