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Reaktionen der Trialkylsilyl-trifluormethansulfonate, X. N-(Trifluoracetyl)-α,β-didehydro-α-aminosäureester durch Trimethylsilanol-Eliminierung aus 2-[(Trifluoracetyl)amino]-3-(trimethylsiloxy)carbonsäureestern (1991)

Seethaler, Toni ; Simchen, Gerhard

Weinheim : Wiley-Blackwell

Liebigs Annalen 1991 (1991), S. 11-17

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ISSN: 0170-2041

Keywords: α-Amino-β-(trimethylsiloxy)carboxylic acid esters, β-elimination ; α,β-Didehydro α-amino acid esters ; Chemistry ; Organic Chemistry

Source: Wiley InterScience Backfile Collection 1832-2000

Topics: Chemistry and Pharmacology

Notes: Reactions of Trialkylsilyl Trifluoromethanesulfonates, X. - N-(Trifluoroacetyl)-α,β-didehydro-α-amino Carboxylic Acid Esters from 2-(Trifluoroacetyl)amino]-3-(trimethylsiloxy)carboxylic Acid Esters by Elimination of Trimethylsilanolα-Amino-β-(trimethylsiloxy)carboxylates 4 are obtained by trimethylsiloxy alkylation of the ketene acetal 1 with aldehydes 2 in the presence of trimethylsilyl triflate (3). β-Elimination of trimethylsilanol from the esters 4 by means of trifluoroacetic acid anhydride (8) or methanesulfonic acid anhydride (15) yields (Z)-didehydro amino acid esters 7. The course of the elimination reaction is studied.

Additional Material: 8 Tab.

Type of Medium: Electronic Resource

URL: http://dx.doi.org/10.1002/jlac.199119910103

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Reaktionen der Trialkylsilyl-trifluormethansulfonate, XII. Aldol-Additionsreaktionen mit 2,6-Bis(trimethylsiloxy)thiophen-Synthese bicyclischer γ-Lactone (1992)

Rzehak, Werner ; Simchen, Gerhard

Weinheim : Wiley-Blackwell

Liebigs Annalen 1992 (1992), S. 615-620

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ISSN: 0170-2041

Keywords: Thiophenes ; 3,7-Dioxabicyclo[3.3.0]octanes ; Aldol additions ; Lactones ; Chemistry ; Organic Chemistry

Source: Wiley InterScience Backfile Collection 1832-2000

Topics: Chemistry and Pharmacology

Notes: Reactions of Trialkylsilyl Trifluoromethanesulfonates, XII. - Aldol-Type Reactions with 2,6-Bis(trimethylsiloxy)thiophene Synthesis of Bicyclic γ-LactonesIn the presence of trimethylsilyl triflate (2) aromatic aldehydes 4 react with 2,6-bis(trimethylsiloxy)thiophene (3) to yield the 3,4-disubstituted thiosuccinic anhydrides 5. By hydrolysis of the products 5 in the presence of lead acetate the diaryl-substituted cis-bislactones 8 are obtained. Dialkyl-substituted cis-bislactones 10 are formed in a aldol addition of aliphatic aldehydes 9 to 3 catalysed by zinc chloride and subsequent hydrolysis of the intermediates. The synthesis of 3,4-bis(dialkoxyalkyl)thiosuccinic anhydrides 7 is achieved by the reaction of 3 with carboxylic acid orthoesters 6 catalysed by 2.

Additional Material: 11 Tab.

Type of Medium: Electronic Resource

URL: http://dx.doi.org/10.1002/jlac.1992199201105

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