Synthesis and reactivities of enantiomerically pure β hydroxyalkyl and β-aminoalkyl ferrocenyl sulfides

Luca Bernardi; Bianca F. Bonini; Mauro Comes-Franchini; Mariafrancesca Fochi; Germana Mazzanti; Alfredo Ricci; Greta Varchi

doi:10.1002/1099-0690(200208)2002:16<2776::AID-EJOC2776>3.0.CO;2-Y

Synthesis and reactivities of enantiomerically pure β hydroxyalkyl and β-aminoalkyl ferrocenyl sulfides

Luca Bernardi, Bianca F. Bonini, Mauro Comes-Franchini, Mariafrancesca Fochi, Germana Mazzanti, Alfredo Ricci, Greta Varchi

Houston Methodist

Research output: Contribution to journal › Article › peer-review

32 Scopus citations

Abstract

Enantiomerically pure β-hydroxyalkyl and β-aminoalkyl ferrocenyl sulfides have been synthesized in good yields from mercaptoferrocene and amino alcohol derivatives. Primary β-aminoalkyl sulfides allowed the synthesis of tetrahydro-1,4-thiazepines containing the ferrocene moiety with good diastereoselectivity and β-iminoalkyl sulfides. Some of these derivatives have successfully been employed as ligands for palladium-catalyzed allylic substitution, with asymmetric induction of up to 99% ee. (

Original language	English (US)
Pages (from-to)	2776-2784
Number of pages	9
Journal	European Journal of Organic Chemistry
Issue number	16
DOIs	https://doi.org/10.1002/1099-0690(200208)2002:16<2776::AID-EJOC2776>3.0.CO;2-Y
State	Published - Aug 2002

Keywords

Allylic substitution
Catalysis
Ferrocene
Palladium
Sandwich complexes
Sulfur

ASJC Scopus subject areas

Physical and Theoretical Chemistry
Organic Chemistry

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10.1002/1099-0690(200208)2002:16<2776::AID-EJOC2776>3.0.CO;2-Y

Cite this

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title = "Synthesis and reactivities of enantiomerically pure β hydroxyalkyl and β-aminoalkyl ferrocenyl sulfides",

abstract = "Enantiomerically pure β-hydroxyalkyl and β-aminoalkyl ferrocenyl sulfides have been synthesized in good yields from mercaptoferrocene and amino alcohol derivatives. Primary β-aminoalkyl sulfides allowed the synthesis of tetrahydro-1,4-thiazepines containing the ferrocene moiety with good diastereoselectivity and β-iminoalkyl sulfides. Some of these derivatives have successfully been employed as ligands for palladium-catalyzed allylic substitution, with asymmetric induction of up to 99\% ee. (",

keywords = "Allylic substitution, Catalysis, Ferrocene, Palladium, Sandwich complexes, Sulfur",

author = "Luca Bernardi and Bonini, \{Bianca F.\} and Mauro Comes-Franchini and Mariafrancesca Fochi and Germana Mazzanti and Alfredo Ricci and Greta Varchi",

year = "2002",

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doi = "10.1002/1099-0690(200208)2002:16<2776::AID-EJOC2776>3.0.CO;2-Y",

language = "English (US)",

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journal = "European Journal of Organic Chemistry",

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TY - JOUR

T1 - Synthesis and reactivities of enantiomerically pure β hydroxyalkyl and β-aminoalkyl ferrocenyl sulfides

AU - Bernardi, Luca

AU - Bonini, Bianca F.

AU - Comes-Franchini, Mauro

AU - Fochi, Mariafrancesca

AU - Mazzanti, Germana

AU - Ricci, Alfredo

AU - Varchi, Greta

PY - 2002/8

Y1 - 2002/8

N2 - Enantiomerically pure β-hydroxyalkyl and β-aminoalkyl ferrocenyl sulfides have been synthesized in good yields from mercaptoferrocene and amino alcohol derivatives. Primary β-aminoalkyl sulfides allowed the synthesis of tetrahydro-1,4-thiazepines containing the ferrocene moiety with good diastereoselectivity and β-iminoalkyl sulfides. Some of these derivatives have successfully been employed as ligands for palladium-catalyzed allylic substitution, with asymmetric induction of up to 99% ee. (

AB - Enantiomerically pure β-hydroxyalkyl and β-aminoalkyl ferrocenyl sulfides have been synthesized in good yields from mercaptoferrocene and amino alcohol derivatives. Primary β-aminoalkyl sulfides allowed the synthesis of tetrahydro-1,4-thiazepines containing the ferrocene moiety with good diastereoselectivity and β-iminoalkyl sulfides. Some of these derivatives have successfully been employed as ligands for palladium-catalyzed allylic substitution, with asymmetric induction of up to 99% ee. (

KW - Allylic substitution

KW - Catalysis

KW - Ferrocene

KW - Palladium

KW - Sandwich complexes

KW - Sulfur

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DO - 10.1002/1099-0690(200208)2002:16<2776::AID-EJOC2776>3.0.CO;2-Y

M3 - Article

AN - SCOPUS:0036677495

SN - 1434-193X

SP - 2776

EP - 2784

JO - European Journal of Organic Chemistry

JF - European Journal of Organic Chemistry

IS - 16

ER -

Synthesis and reactivities of enantiomerically pure β hydroxyalkyl and β-aminoalkyl ferrocenyl sulfides

Abstract

Keywords

ASJC Scopus subject areas

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