The diastereoselective ortho-lithiation of Kagan’s ferrocenyl acetal. Generation and reactivity of chiral 2-substituted ferrocenecarboxaldehydes

This review focuses on the synthesis of enantiopure ferrocenyl compounds using Kagan’s acetal 3 as the starting material. The lithiation of 3 is highly diastereoselective furnishing after removal of the chiral auxiliary 2-substituted ferrocenecarboxaldehydes with high ees. Special attention is given to the chemical transformations allowed by the presence of the aldehyde functionality. Applications of the final products in asymmetric catalysis, material chemistry, and biology are also discussed.

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