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Synthesis of Three-, Five-, and Six-Membered Heterocycles Derived from New β-Amino-α-trifluoromethyl Alcohols


Heimgartner, H; Linden, A; Mloston, G; Obijalska, E (2010). Synthesis of Three-, Five-, and Six-Membered Heterocycles Derived from New β-Amino-α-trifluoromethyl Alcohols. Helvetica Chimica Acta, 93(9):1725-1736.

Abstract

Nucleophilic trifluoromethylation of α-iminoketones 2, derived from arylglyoxal, with Ruppert-Prakash reagent (CF3SiMe3) offers a convenient access to the corresponding O-silylated β-imino-α-trifluoromethyl alcohols. In a ‘one-pot’ procedure, by treatment with NaBH4, these products smoothly undergo reduction and desilylation yielding the expected β-amino-α-trifluoromethyl alcohols 4. The latter were used as convenient starting materials for the synthesis of diverse trifluoromethylated heterocycles, including aziridines 5, 1,3-oxazolidines 8, 1,3-oxazolidin-2-ones 9, 1,3,2-oxazaphospholidine 2-oxides 10, 1,2,3-oxathiazolidine 2-oxides 11, and morpholine-2,3-diones 12. An optically active 5-trifluoromethyl-substituted 1,3-oxazolidin-2-one 9g was also obtained.

Abstract

Nucleophilic trifluoromethylation of α-iminoketones 2, derived from arylglyoxal, with Ruppert-Prakash reagent (CF3SiMe3) offers a convenient access to the corresponding O-silylated β-imino-α-trifluoromethyl alcohols. In a ‘one-pot’ procedure, by treatment with NaBH4, these products smoothly undergo reduction and desilylation yielding the expected β-amino-α-trifluoromethyl alcohols 4. The latter were used as convenient starting materials for the synthesis of diverse trifluoromethylated heterocycles, including aziridines 5, 1,3-oxazolidines 8, 1,3-oxazolidin-2-ones 9, 1,3,2-oxazaphospholidine 2-oxides 10, 1,2,3-oxathiazolidine 2-oxides 11, and morpholine-2,3-diones 12. An optically active 5-trifluoromethyl-substituted 1,3-oxazolidin-2-one 9g was also obtained.

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Additional indexing

Item Type:Journal Article, refereed, original work
Communities & Collections:07 Faculty of Science > Department of Chemistry
Dewey Decimal Classification:540 Chemistry
Language:English
Date:September 2010
Deposited On:26 Nov 2010 16:16
Last Modified:05 Apr 2016 14:16
Publisher:Verlag Helvetica Chimica Acta
ISSN:0018-019X
Publisher DOI:https://doi.org/10.1002/hlca.201000232

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