Application

No.141,142
Asymmetric Synthesis of Enantiopure 1,2-Disubstituted Ferrocenes
T2545 (R)-(p-Toluenesulfinyl)ferrocene (1a) 1g
5g
T2546 (S)-(p-Toluenesulfinyl)ferrocene (1b) 1g
5g

Kagan et al. have reported the synthesis of planar-chiral 1,2-disubstituted ferrocenes 3 using chiral sulfinyl ferrocenes 1. According to the report, lithiation of 1 by LDA and the following reaction with various electrophiles affords o-substituted products 2. Then, lithiation of 2 by t-BuLi and the following reaction with electrophiles affords planar-chiral 1,2-disubstituted ferrocenes 3 with high stereoselectivity. These ferrocenes are expected to be used for various applications like chiral ligands.

References

A straightforward asymmetric synthesis of enantiopure 1,2-disubstituted ferrocenes
O. Riant, G. Argouarch, D. Guillaneux, O. Samuel, H. B. Kagan, J. Org. Chem. 1998, 63, 3511[DOI].
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