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

Angela Patti; Daniela Lambusta; Mario Piattelli; Giovanni Nicolosi; Patrick McArdle; Desmond Cunningham; Martin Walsh

doi:10.1016/S0040-4020(96)01048-4

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

Angela Patti, Daniela Lambusta, Mario Piattelli, Giovanni Nicolosi, Patrick McArdle, Desmond Cunningham, Martin Walsh

Research output: Contribution to a Journal (Peer & Non Peer) › Article › peer-review

30 Citations (Scopus)

Abstract

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

Original language	English
Pages (from-to)	1361-1368
Number of pages	8
Journal	Tetrahedron
Volume	53
Issue number	4
DOIs	https://doi.org/10.1016/S0040-4020(96)01048-4
Publication status	Published - 27 Jan 1997
Externally published	Yes

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

abstract = "Racemic 2-hydroxymethyl-1-phenylthioferrocene 5 and 2-hydroxymethyl-1-tert-butylthioferrocene 6 were subjected to kinetic resolution via acetylation catalysed by lipase from Candida antarctica (Novozym{\textregistered} 435) or Mucor miehei (Lipozyme{\textregistered} IM). The obtained enantiopure thioethers underwent chemical oxygenation at the sulfur atom to give the corresponding ferrocenyl sulfoxides with settled central/planar chirality.",

author = "Angela Patti and Daniela Lambusta and Mario Piattelli and Giovanni Nicolosi and Patrick McArdle and Desmond Cunningham and Martin Walsh",

year = "1997",

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doi = "10.1016/S0040-4020(96)01048-4",

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TY - JOUR

T1 - Lipase-assisted preparation of enantiopure ferrocenyl sulfides possessing planar chirality and their use in the synthesis of chiral sulfoxides

AU - Patti, Angela

AU - Lambusta, Daniela

AU - Piattelli, Mario

AU - Nicolosi, Giovanni

AU - McArdle, Patrick

AU - Cunningham, Desmond

AU - Walsh, Martin

PY - 1997/1/27

Y1 - 1997/1/27

N2 - Racemic 2-hydroxymethyl-1-phenylthioferrocene 5 and 2-hydroxymethyl-1-tert-butylthioferrocene 6 were subjected to kinetic resolution via acetylation catalysed by lipase from Candida antarctica (Novozym® 435) or Mucor miehei (Lipozyme® IM). The obtained enantiopure thioethers underwent chemical oxygenation at the sulfur atom to give the corresponding ferrocenyl sulfoxides with settled central/planar chirality.

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

UR - https://www.scopus.com/pages/publications/0031033510

U2 - 10.1016/S0040-4020(96)01048-4

DO - 10.1016/S0040-4020(96)01048-4

M3 - Article

SN - 0040-4020

VL - 53

SP - 1361

EP - 1368

JO - Tetrahedron

JF - Tetrahedron

IS - 4

ER -

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

Abstract

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