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Reaction of (trifluoromethyl)trimethylsilane with oxazolidin-5-ones: Synthesis of peptidic and nonpeptidic trifluoromethyl ketones

Abstract:
(Trifluoromethyl)trimethylsilane (TMS-CF3, the Ruppert Reagent) reacts with a variety of amino acid derived N-substituted oxazolidin-5-ones in excellent yields. Mild acid hydrolysis of adducts with electron-releasing substituents at C-2 affords N-substituted α-amino trifluoromethyl ketones (TFMKs). N-CBZ-protected α-amino TFMKs are converted into hitherto unreported hydrochloride salts of α-amino TFMKs by hydrogenolysis. Coupling with amino acid fluorides gives access to peptidic TFMKs which are of utility as protease inhibitors.
Publication status:
Published

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Publisher copy:
10.1021/jo980443+

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Institution:
University of Oxford
Department:
Oxford, MPLS, Chemistry, Organic Chemistry
Role:
Author
Journal:
JOURNAL OF ORGANIC CHEMISTRY
Volume:
63
Issue:
15
Pages:
5179-5192
Publication date:
1998-07-24
DOI:
EISSN:
1520-6904
ISSN:
0022-3263
URN:
uuid:300b66f6-5625-4e79-a73b-737735105e44
Source identifiers:
36659
Local pid:
pubs:36659
Language:
English

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