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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
Author(s) -
Seethaler Toni,
Simchen Gerhard
Publication year - 1991
Publication title -
liebigs annalen der chemie
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 0170-2041
DOI - 10.1002/jlac.199119910103
Subject(s) - chemistry , ketene , trifluoroacetic anhydride , trimethylsilyl trifluoromethanesulfonate , trimethylsilyl , acetal , methanesulfonic acid , silylation , organic chemistry , alkylation , acylation , medicinal chemistry , catalysis
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 Trimethylsilanol α‐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.