An Efficient Asymmetric Synthesis of 2-Substituted Ferrocenecarboxaldehydes
(1997) The Journal of Organic Chemistry — Vol. 63, p. 6733 (1997)
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- Abstract
- Ferrocenecarboxaldehyde is readily transformed into the acetal of (S)-1,2,4-butanetriol (1,3-dioxane structure) and further methylated to give acetal 15. This can then be ortho-lithiated using t-BuLi with very high diastereoselectivity (98% de). Electrophilic quenching provided a large array of compounds of established stereochemistry. Controlled hydrolysis leads to many ortho-substituted ferrocenecarboxaldehydes (98% ee) which themselves are starting materials in the synthesis of various classes of enantiopure ferrocene derivatives with planar chirality of predictable absolute configuration.
- Affiliations
Université Paris-Sud (France) Chimie organique
Citations
Riant, O., Samuel, O., Flessner, T., Taudien, S., & Kagan, H. B. (1997). An Efficient Asymmetric Synthesis of 2-Substituted Ferrocenecarboxaldehydes. The Journal of Organic Chemistry, 63, 6733. https://doi.org/10.1021/jo970075u (Original work published 1997)