Synthesis and reactivity of achiral and of a novel planar chiral thioferrocenoylsilanes

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

doi:10.1016/S0022-328X(01)00944-5

Synthesis and reactivity of achiral and of a novel planar chiral thioferrocenoylsilanes

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

Houston Methodist

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

16 Scopus citations

Abstract

The reactions of thioferrocenoylsilanes with organolithium reagents, dienes and reducing agents which afford α-silyl sulphides, dihydrothiopyranes and α-silyl ferrocenyl thiols, respectively, have been investigated. α-Silyl sulphides were further functionalised through carbodesilylation with aldehydes. We also report the synthesis of a new planar chiral thioferrocenoylsilane that gave good diastereomeric excess in the reaction with t-butyllithium, lithium lutidine and 2,3-dimethylbuta-1,3-diene. The 1,1′-bis-thioferrocenoylsilane, too unstable to be isolated, was trapped in situ with dienes.

Original language	English (US)
Pages (from-to)	407-417
Number of pages	11
Journal	Journal of Organometallic Chemistry
Volume	637-639
DOIs	https://doi.org/10.1016/S0022-328X(01)00944-5
State	Published - Dec 3 2001

Keywords

Diels-Alder reaction
Ferrocene
Planar chirality
Thioacylsilanes
Thiophilic addition
β-Amino sulphides
β-Hydroxy sulphides

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry
Inorganic Chemistry
Materials Chemistry

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10.1016/S0022-328X(01)00944-5

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title = "Synthesis and reactivity of achiral and of a novel planar chiral thioferrocenoylsilanes",

abstract = "The reactions of thioferrocenoylsilanes with organolithium reagents, dienes and reducing agents which afford α-silyl sulphides, dihydrothiopyranes and α-silyl ferrocenyl thiols, respectively, have been investigated. α-Silyl sulphides were further functionalised through carbodesilylation with aldehydes. We also report the synthesis of a new planar chiral thioferrocenoylsilane that gave good diastereomeric excess in the reaction with t-butyllithium, lithium lutidine and 2,3-dimethylbuta-1,3-diene. The 1,1′-bis-thioferrocenoylsilane, too unstable to be isolated, was trapped in situ with dienes.",

keywords = "Diels-Alder reaction, Ferrocene, Planar chirality, Thioacylsilanes, Thiophilic addition, β-Amino sulphides, β-Hydroxy sulphides",

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

note = "Funding Information: This work has been supported by University of Bologna (Funds for Selected Research Topics, A.A. 1999–2001) and by the National Project {\textquoteleft}Stereoselezione in Sintesi Organica. Metodologie ed Applicazioni 1999–2001{\textquoteright}. Copyright: Copyright 2007 Elsevier B.V., All rights reserved.",

year = "2001",

month = dec,

day = "3",

doi = "10.1016/S0022-328X(01)00944-5",

language = "English (US)",

volume = "637-639",

pages = "407--417",

journal = "Journal of Organometallic Chemistry",

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TY - JOUR

T1 - Synthesis and reactivity of achiral and of a novel planar chiral thioferrocenoylsilanes

AU - Bonini, Bianca F.

AU - Comes-Franchini, Mauro

AU - Fochi, Mariafrancesca

AU - Mazzanti, Germana

AU - Ricci, Alfredo

AU - Tomasulo, Massimiliano

AU - Varchi, Greta

N1 - Funding Information: This work has been supported by University of Bologna (Funds for Selected Research Topics, A.A. 1999–2001) and by the National Project ‘Stereoselezione in Sintesi Organica. Metodologie ed Applicazioni 1999–2001’. Copyright: Copyright 2007 Elsevier B.V., All rights reserved.

PY - 2001/12/3

Y1 - 2001/12/3

N2 - The reactions of thioferrocenoylsilanes with organolithium reagents, dienes and reducing agents which afford α-silyl sulphides, dihydrothiopyranes and α-silyl ferrocenyl thiols, respectively, have been investigated. α-Silyl sulphides were further functionalised through carbodesilylation with aldehydes. We also report the synthesis of a new planar chiral thioferrocenoylsilane that gave good diastereomeric excess in the reaction with t-butyllithium, lithium lutidine and 2,3-dimethylbuta-1,3-diene. The 1,1′-bis-thioferrocenoylsilane, too unstable to be isolated, was trapped in situ with dienes.

AB - The reactions of thioferrocenoylsilanes with organolithium reagents, dienes and reducing agents which afford α-silyl sulphides, dihydrothiopyranes and α-silyl ferrocenyl thiols, respectively, have been investigated. α-Silyl sulphides were further functionalised through carbodesilylation with aldehydes. We also report the synthesis of a new planar chiral thioferrocenoylsilane that gave good diastereomeric excess in the reaction with t-butyllithium, lithium lutidine and 2,3-dimethylbuta-1,3-diene. The 1,1′-bis-thioferrocenoylsilane, too unstable to be isolated, was trapped in situ with dienes.

KW - Diels-Alder reaction

KW - Ferrocene

KW - Planar chirality

KW - Thioacylsilanes

KW - Thiophilic addition

KW - β-Amino sulphides

KW - β-Hydroxy sulphides

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U2 - 10.1016/S0022-328X(01)00944-5

DO - 10.1016/S0022-328X(01)00944-5

M3 - Article

AN - SCOPUS:0035803778

SN - 0022-328X

VL - 637-639

SP - 407

EP - 417

JO - Journal of Organometallic Chemistry

JF - Journal of Organometallic Chemistry

ER -

Synthesis and reactivity of achiral and of a novel planar chiral thioferrocenoylsilanes

Abstract

Keywords

ASJC Scopus subject areas

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