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Digitale Medien

C,C-Verknüpfungen mit Schwefel-stabilisierten Carbanionen, 2[1] Reaktionen des 2-(Methylthio)thiolan-Carbanions mit Elektrophilen[2] (1992)

Böge, Askan ; Brunck, Jörg-Stephan ; Schwär, Gerhard ; [weitere]

Weinheim : Wiley-Blackwell

Berichte der deutschen chemischen Gesellschaft 125 (1992), S. 1641-1646

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ISSN: 0009-2940

Schlagwort(e): Thioacetals, semicyclic ; Carbanions ; Alkylation ; Hydroxyalkylation ; Diastereoselectivity ; Thiolanes ; Chemistry ; Inorganic Chemistry

Quelle: Wiley InterScience Backfile Collection 1832-2000

Thema: Chemie und Pharmazie

Notizen: C,C Coupling with Sulfur-Stabilized Carbanions, 2[1]. - Reactions of the 2-(Methylthio)thiolane Carbanion with Electrophiles[2]The „semicyclic” thioacetal 2-(methylthio)thiolane (4) is easily prepared from thiolane (tetrahydrothiophene). It is readily deprotonated by butyllithium to give the lithium derivative 5, which reacts with alkyl halides, saturated and α,β-unsaturated carbonyl compounds, and benzonitrile to form the alkyl derivatives 6, carbinols 7, allyl alcohols 8, and - after hydrolysis - the ketone 9. The diastereoselectivity of the C,C coupling reaction is discussed.

Materialart: Digitale Medien

URL: http://dx.doi.org/10.1002/cber.19921250720

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Digitale Medien

Formation of δ-Sultines (1,2-Oxathiane 2-Oxides) from Thiolane 1-Oxides (1999)

Schuler, Barbara ; Voss, Jürgen

Weinheim : Wiley-Blackwell

Liebigs Annalen 1999 (1999), S. 943-947

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ISSN: 1434-193X

Schlagwort(e): Thiolane 1-oxides ; Oxidations ; δ-Sultines ; [Bis(trifluoroacetoxy)iodo]benzene ; Asymmetric synthesis ; Carbanions ; Chemistry ; General Chemistry

Quelle: Wiley InterScience Backfile Collection 1832-2000

Thema: Chemie und Pharmazie

Notizen: -2-(Alkylthio)-2-benzylthiolane 1-oxides (1a, b) and 2-(alkylthio)-2-(α-hydroxybenzyl)thiolane 1-oxides (1c, d) are oxidized with [bis(trifluoroacetoxy)iodo]benzene (PIFA). Under ring enlargement the corresponding cyclic sulfinate esters (δ-sultines) 2 are formed. Only (1R*,2S*)-1b is reactive whereas (1R*,2R*)-1b is not attacked. This observation is explained with the formation of a cyclic intermediate 3.

Materialart: Digitale Medien

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Digitale Medien

Reaction of the Carbanions of 2-(Alkylthio)thiolane 1-Oxides with Oxiranes (1999)

Schuler, Barbara ; Adiwidjaja, Gunadi ; Voss, Jürgen

Weinheim : Wiley-Blackwell

Liebigs Annalen 1999 (1999), S. 1481-1488

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ISSN: 1434-193X

Schlagwort(e): Thiolane 1-oxides ; Carbanions ; Oxiranes ; Asymmetric synthesis ; X-ray structure ; Chemistry ; General Chemistry

Quelle: Wiley InterScience Backfile Collection 1832-2000

Thema: Chemie und Pharmazie

Notizen: -Carbanions of the 2-(alkylthio)thiolane 1-oxides 1 and 2 are generated and subjected to reaction with the epoxides 3-5. The resulting carbinols 6-11 are formed with high α diastereoselectivity, which is explained by a stabilization of the trans configuration of the carbanions in the activated complex. A minor γ stereoselectivity is also observed in case of the reactions with 4 and 5. The pure enantiomers (1S,2S,2′S)-9a and (1R,2R,2′S)-11b were obtained from 2 and (S)-4 or (R)-5, respectively, and their configurations were proved by X-ray structural analyses.

Zusätzliches Material: 2 Ill.

Materialart: Digitale Medien

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