Chemoenzymatic synthesis of optically active 1,2-disubstituted ferrocenes with planar chirality
(2009) Tetrahedron: Asymmetry — Vol. 20, n° 12, p. 1371-1377 (2009)
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- A new pathway for the synthesis of 2-substituted ferrocenyl compounds with planar chirality using a chemoenzymatic resolution as the key step is described. The kinetic resolution of racemic 2-hydroxy-methyl phenylthioferrocene 4 has been optimised and carried Out on a multi-gram scale using CAL-B lipase, giving the resulting acetate and remaining alcohols in ee's >99%. The enantiomerically enriched sulfides have been transformed via a two-step sequence, in a new family of 2-substituted ferrocenyl alcohol by using a sulfoxide-lithium exchange/electrophilic trapping sequence; this gives straightforward access to non-racemic ferrocenyl alcohols with planar chirality. (C) 2009 Elsevier Ltd. All rights reserved.
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Merabet-Khellasi, M., Aribi-Zouioueche, L., & Riant, O. (2009). Chemoenzymatic synthesis of optically active 1,2-disubstituted ferrocenes with planar chirality. Tetrahedron: Asymmetry, 20(12), 1371-1377. https://doi.org/10.1016/j.tetasy.2009.04.014 (Original work published 2009)