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Lipase-assisted preparation of enantiopure ferrocenyl sulfides possessing planar chirality and their use in the synthesis of chiral sulfoxides

โœ Scribed by Angela Patti; Daniela Lambusta; Mario Piattelli; Giovanni Nicolosi; Patrick McArdle; Desmond Cunningham; Martin Walsh

Book ID
104207425
Publisher
Elsevier Science
Year
1997
Tongue
French
Weight
445 KB
Volume
53
Category
Article
ISSN
0040-4020

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โœฆ Synopsis

Racernic 2-hydroxymethyl-l-phenylthioferrocane 5 and 2-hydroxymethyl-1tert-butylthioferrocene 6 were subjected to kinetic resolution via acetylation catalysed by lipase from Candida antarctica (Novozym ยฎ 435) or Mucor miehei (Lipozyrne ยฎ IM). The obtained enantiopure thioethers underwent chemical oxygenation at the sulfur atom to give the corresponding ferrocenyl sulfoxides with settled central/planar chirality.

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We have shown that cymantrene derivatives are better P,N-chelate ligands for palladium-catalyzed allylic alkylation than ferrocenes, which have a similar pentagonal ligand structure to cymantrene derivatives. In particular, the PPh 3 -substituted cymantrene gave a higher enantioselectivity (>98%).