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

Consiglio Nazionale delle Ricerche
University of Galway

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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pages = "1361--1368",

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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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